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CAS No. : | 103478-62-2 | MDL No. : | MFCD00151933 |
Formula : | C22H25NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BUJQSIPFDWLNDC-FQEVSTJZSA-N |
M.W : | 367.44 | Pubchem ID : | 7015835 |
Synonyms : |
Fmoc-N-Me-Leu-OH
|
Chemical Name : | Fmoc-N-Me-Leu-OH |
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 104.49 |
TPSA : | 66.84 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.3 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 4.56 |
Log Po/w (WLOGP) : | 4.37 |
Log Po/w (MLOGP) : | 3.22 |
Log Po/w (SILICOS-IT) : | 3.51 |
Consensus Log Po/w : | 3.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.79 |
Solubility : | 0.00593 mg/ml ; 0.0000162 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.69 |
Solubility : | 0.000756 mg/ml ; 0.00000206 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.37 |
Solubility : | 0.00156 mg/ml ; 0.00000426 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.97 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Two different tetrapeptides - Leu-Ala- Val-Gly-D-HomoPhe and Ala-Tyr(tBu)-N- MeLeu-Gly-D-HomoPhe were synthesized using standard solid phase coupling protocols. The mimic FKBD substrate was coupled to the terminal D-homophenylalanine followed by activation with ICH2CN in absence of light and subsequent removal of all Boc protecting groups using 50-80 % TFA in DCM. This was followed by the macrolactamization with 20% DIPEA in THF and cyclitive release of the desired mimic rapafucin in 20-28 % yield after purification. Synthesis of one of the peptide sequences is shown in Scheme 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Synthesis of linear peptide was carried out using 2-chlorotrityl chloride (CTC) resin (1.05 mmol/g)following the standard Fmoc strategy. All reactions were performed on 0.250 g of resin scale.First N-Fmoc protected aa (2 eq.) residue was coupled with CTC resin (0.250 g) using DIPEA(4 eq.) in DCM (5 mL) for 2 h at rt. After filtration, the remaining unreacted sites were cappedby a solution of DCM/MeOH/DIPEA (4:5:1, 10 mL) for 30 min. Resin was washed with DCM(3 5 mL), N,N-Dimethylformamide (DMF) (3 5 mL) MeOH (3 5 mL). Deprotection of Fmocgroup was carried out using 20% piperidine in DMF for (2 10 min) at rt. Loading of resin wasmeasured by concentration of Fmoc group by ultraviolet standard curve method. The first aa boundresin was thoroughly washed with DCM (3 5 mL), DMF (3 5 mL) and MeOH (3 5 mL). All otherN-Fmoc aa (2.0 eq.) coupling, including N-Me were carried out using standard solid phase peptidesynthesis using DEPBT (2.0 eq.) as coupling reagent in the presence of DIPEA (2 eq.) in DMF/DCM(1:1, 5 mL) at rt for 3 h. Reaction was monitored using Kaiser test for the primary amine and chloraniltest for the secondary amine. Generally, coupling with N-Me aa took 5-6 h further time to complete thereaction. Cleavage was performed using 1% TFA in DCM for (2 30 min) at rt. After cleavage, filtratewas immediately neutralized with 1% pyridine in MeOH and concentrated under reduced pressure.Crude peptide was isolated via precipitation from diethylether (20 mL), collected through centrifugeas a white solid, which can be directly used for macrocyclisation reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Fmoc-amide resin (0.40 g, 0.25 mmol) was placed in a reaction vessel equipped with a glass filter, and 15 mL of 20percent piperidine in NMP was added thereto and shaken for 20 minutes, thus removing the Fmoc group. Thereafter, 15 mL NMP, 1.0 mmol (4 equivalents) of Fmoc-MeLeu-OH, 1.0 mmol (4 equivalents) of TBTU, 1.0 mmol (4 equivalents) of HOBt and 1.0 mmol (4 equivalents) of DIPEA were added thereto and shaken for 1 hour to condense the Fmoc-MeLeu. Thereafter, the peptide chain was extended by repeatedly carrying out removal of Fmoc group by 20percent piperidine and condensation of Fmoc-amino acid (3 equivalents) by bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (3 equivalents) in the presence of 2.25 mmol (9 equivalents) of DIPEA. The conclusion of the condensation reaction was confirmed by deprotecting a small amount of the resin with TFA and examining it by HPLC and mass spectrometry (MS). After Boc-NH?(CH2)4?CO-Ser (O?C8H17)-MePhe-MeLeu-resin was obtained, this resin was treated with TFA for 30 minutes, whereby the resin was cleaved to de-protect the peptide. After the TFA was evaporated, the peptide was washed with ether (Et2O) to give 120 mg NH2?(CH2)4?CO-Ser(C8H17)-MePhe-MeLeu-NH2. This product was applied to YMC-Pack ODS-A (C18, 20 mm×250 mm) and eluted with a linear gradient (flow rate: 10 mL/min.) for 60 minutes of 0 to 54percent acetonitrile in 0.1percent trifluoroacetic acid. The desired fractions were collected and lyophilized to give 70 mg of the desired product. After this derivative was hydrolyzed with propionic acid-HCl (50/50) at 150° C. for 2 hours, the amount of the peptide was quantified using the ratio of the peak area of aminopentanoic acid detected in the amino acid analyzer to that of 10 nmol aminopentanoic acid as a standard. ESI-MS [M+H]; 604.5 (theoretical: 603.8), detected amino acids after hydrolysis with propionic acid?HCl (50/50) at 150° C. for 2 hours: Ser, Ape. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.5 eq of commercially available Fmoc-NH-OH and DIEA (10 eq) are added to the 2-chlorotrityl resin in 2 mL DCM. The mixture is intermittently stirred manually during 24h. After that, 0.5 mL/g of MeOH are added to the reaction mixture to cap the remaining reactive points of the resin. After 15 minutes, the solution is filtered off and the resin is washed thoroughly with DCM, DMF and MeOH. Fmoc removal is achieved by treating the resin with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). For the coupling of Na-Fmoc-NY-alloc-L-2,4-diaminobutyric acid (Fmoc-L-Dab(alloc)-OH), 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. To extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15 '). After that, Fmoc- N-methyl-L-iso leucine (Fmoc-NMe-L-Ile-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15 '). After that, Fmoc- L-Proline (Fmoc-L-Pro-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting the mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15') and additional treatment with a mixture of piperidine/DBU/toluene/DMF (5:5:20:70) (1 x 5'). After that, Fmoc-N- methyl-L-leucine (Fmoc-NMeLeu-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). After that, Na- Fmoc-N(in)-Boc-N-methyl-L-tryptophan (Fmoc-NMe-L-Trp(Boc)-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). Butiric acid is coupled to the tryptophan moiety by adding to the resin 3 eq of the acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting the mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. Then the reaction is filtered off and the resin is rinsed thoroughly with DMF and DCM. The extent of the reaction is monitored using the chloranil test. For the removal of the Alloc group, 10 eq of phenylsilane in DCM are added to the resin while N2 is bubbled through the mixture. Then, 0.1 eq of Pd(PPli3)4 are added maintaining the N2 bubbling while mixing everything well. Then the reaction vessel is sealed and shaken for 15 minutes. After this time, the reaction is filtered and the resin washed thoroughly. The same treatment is repeated two more times. After the last treatment, the resin is washed thoroughly with DCM, MeOH and DMF. For the coupling of the 3,5-difluorobenzoic acid on the side chain of the diaminoethyl moiety, 3 eq of said acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. After this time, the resin is washed with DMF and DCM and the extent of the reaction is monitored the Kaiser test. For the cleavage of the peptide, the resin is washed several times with DCM and dried by suction. The peptide is cleaved from the resin by adding a solution of DCM/TFA (95:5), the mixture is allowed to react for 15 min. Then the reaction mixture is filtered and the resin rinsed with DCM. This cleavage procedure is repeated twice. All the filtrates are pooled and the solvent is evaporated under vacuum, yielding example 14. The compound is purified using reverse-phase chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Linear peptomers were synthesized on L-phenylalanine 2-chlorotrityl resin (0.14 mmol/g) using extended Fmoc coupling (Fmoc amino acid/HATU/DIPEA in DMF, overnight) and peptoid synthesis conditions (bromoacetic acid/DIC in DMF, 1hr, then amine in DMF, overnight). The linear peptomers were cleaved from resin with 30% HFIP in DCM. Cyclization was performed in dilute conditions (<3 mM peptomer in a solution of 1:1 ACN:THF) with COMU (2 equiv) and DIPEA (10 equiv) and stirred overnight at room temperature. Each sub-library was briefly purified using Isolute 103 SPE cartridge (200 mg/6 mL, Biotage).Fmoc deprotectionTwo resin-volumes of 2% DBU 2% piperidine in DMF were added to the resin and the tube was capped and agitated for 20 min. The resin was then drained and washed with 2 resin-volumes of DMF (x3) and 2 resin-volumes of DCM (x3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Linear peptomers were synthesized on L-phenylalanine 2-chlorotrityl resin (0.14 mmol/g) using extended Fmoc coupling (Fmoc amino acid/HATU/DIPEA in DMF, overnight) and peptoid synthesis conditions (bromoacetic acid/DIC in DMF, 1hr, then amine in DMF, overnight). The linear peptomers were cleaved from resin with 30% HFIP in DCM. Cyclization was performed in dilute conditions (<3 mM peptomer in a solution of 1:1 ACN:THF) with COMU (2 equiv) and DIPEA (10 equiv) and stirred overnight at room temperature. Each sub-library was briefly purified using Isolute 103 SPE cartridge (200 mg/6 mL, Biotage).Fmoc deprotectionTwo resin-volumes of 2% DBU 2% piperidine in DMF were added to the resin and the tube was capped and agitated for 20 min. The resin was then drained and washed with 2 resin-volumes of DMF (x3) and 2 resin-volumes of DCM (x3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Linear peptomers were synthesized on L-phenylalanine 2-chlorotrityl resin (0.14 mmol/g) using extended Fmoc coupling (Fmoc amino acid/HATU/DIPEA in DMF, overnight) and peptoid synthesis conditions (bromoacetic acid/DIC in DMF, 1hr, then amine in DMF, overnight). The linear peptomers were cleaved from resin with 30% HFIP in DCM. Cyclization was performed in dilute conditions (<3 mM peptomer in a solution of 1:1 ACN:THF) with COMU (2 equiv) and DIPEA (10 equiv) and stirred overnight at room temperature. Each sub-library was briefly purified using Isolute 103 SPE cartridge (200 mg/6 mL, Biotage).Fmoc deprotectionTwo resin-volumes of 2% DBU 2% piperidine in DMF were added to the resin and the tube was capped and agitated for 20 min. The resin was then drained and washed with 2 resin-volumes of DMF (x3) and 2 resin-volumes of DCM (x3). |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
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P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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