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CAS No. : | 71989-35-0 | MDL No. : | MFCD00077075 |
Formula : | C23H27NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 397.46 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.39 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 110.33 |
TPSA : | 84.86 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.91 cm/s |
Log Po/w (iLOGP) : | 2.79 |
Log Po/w (XLOGP3) : | 3.96 |
Log Po/w (WLOGP) : | 4.18 |
Log Po/w (MLOGP) : | 2.62 |
Log Po/w (SILICOS-IT) : | 3.59 |
Consensus Log Po/w : | 3.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.51 |
Solubility : | 0.0122 mg/ml ; 0.0000308 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.44 |
Solubility : | 0.00143 mg/ml ; 0.00000361 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.83 |
Solubility : | 0.000583 mg/ml ; 0.00000147 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 4.49 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
Lys(Boc)-Pra-Asn(Trt)-Thr(tBu)-Ala-Thr(tBu)-Ala(N3)-Ala-Pal-PEG resin (16) (0.498 g, 0.09 mmol) was cleaved with TFA/iPr3SiH/H2O (v/v/v; 95/2.5/2.5, 5.0 mL) for 2 h, peptide was isolated as described in the general section to afford 47.3 mg of crude peptide 17. The crude peptide 17 (16.3 mg) was purified by RP-HPLC on a preparative Phenomenex Gemini C18, column at a flow rate of 5 mL min-1, using a linear gradient of 1percentB to 61percentB over 60 min (ca. 1percentB per minute) and lyophilised to give the title compound 17 as a white amorphous solid (4.9 mg, 18percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Lys(Boc)-Pra-Asn(Trt)-Thr(tBu)-Ala-Thr(tBu)-Ala(N3)-Ala-Pal-PEG resin (16) (0.498 g, 0.09 mmol) was cleaved with TFA/iPr3SiH/H2O (v/v/v; 95/2.5/2.5, 5.0 mL) for 2 h, peptide was isolated as described in the general section to afford 47.3 mg of crude peptide 17. The crude peptide 17 (16.3 mg) was purified by RP-HPLC on a preparative Phenomenex Gemini C18, column at a flow rate of 5 mL min-1, using a linear gradient of 1percentB to 61percentB over 60 min (ca. 1percentB per minute) and lyophilised to give the title compound 17 as a white amorphous solid (4.9 mg, 18percent). Purified Lys-Pra-Asn-Thr-Ala-Thr-Ala(N3)-Ala-NH2 (17) (4.4 mg, 5.42 x 10-3 mmol) was dissolved in a mixture of water and tert-butyl alcohol (1 : 2.5, 3.5 mL in total). A stock solution of CuSO4 (0.87 mg, 5.42 x 10-3 mmol) and sodium ascorbate (2.68 mg, 13.6 x 10-3 mmol) in water (1.5 mL) was added and the mixture was microwaved for 20 min at 80 °C in a sealed reaction vessel (120 W max) to afford crude peptide (8), containing inseparable dehydroalanine by-product. The crude peptide (8) was purified by RP-HPLC on a preparative Waters XTerra.(R). Prep. C18 column at a flow rate of 10 mL/min, using a linear gradient of 1percentB to 51percentB over 50 min (ca. 1percentB per minute). Fractions were lyophilised to give the title compound 8 as a white amorphous solid (0.7 mg, 18percent), containing inseparable dehydroalanine by-product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Fmoc SPPS was performed on a Liberty Microwave Peptide Synthesiser (CEM Corporation, Mathews, NC) using the Fmoc/tBu strategy as previously described35 or manually starting from PAL-PEG polystyrene resin (0.21 mmol/g). For manual synthesis the following steps were undertaken: (a) Fmoc deprotection with 20percent piperidine for 5 min, then 15 min, washing with DMF 5.x.; (b) coupling of the Fmoc amino acid (5 equiv) in the presence of HBTU in DMF (4.9 equiv) and iPr2NEt (10 equiv) for 1 h and washing with DMF 5.x.. For coupling of Fmoc-Pra (1.5 equiv) and Fmoc-N3Ala (1.5 equiv), 1.45 equiv of HBTU and 4.5 equiv of iPr2NEt were used. The progress of the acylation step was monitored by the Kaiser test. A minimum amount of DMF was used for dissolution of the Fmoc amino acid. The resulting peptides were cleaved from the resin with simultaneous side chain protecting group removal by treatment with either TFA/iPr3SiH/DODT/H2O (v/v/v/v; 94/1/2.5/2.5), or with TFA/iPr3SiH/H2O (v/v/v; 95/2.5/2.5) for 2 h at room temperature. Crude peptides were precipitated and triturated with cold diethyl ether, isolated (centrifugation), dissolved in 20percent acetonitrile (aq) containing 0.1percent TFA and lyophilized. Analytical RP-HPLC was performed using a Dionex P680 (flow rate of 1 mL/min), or Dionex Ultimate U3000 system (flow rate of 0.5 mL/min or 0.2 mL/min) using Waters XTerra.(R). column (MS C18, 150 mm .x. 4.6 mm; 5 mum) or, Phenomenex Aqua column (C18, 250 mm .x. 4.6 mm; 5mu), or Phenomenex, Gemini column (C18, 50 mm .x. 2.0 mm, 5mu), using gradient systems as indicated in the Supplementary data. The solvent system used was A (0.1percent TFA in H2O) and B (0.1percent TFA in acetonitrile) with detection at 210 nm, 254 nm, and 280 nm****. The ratio of products was determined by integration of spectra recorded at 210 nm. Peptide masses were confirmed by an inline Thermo Finnegan MSQ mass spectrometer using ESI in the positive mode. When appropriate, a Bruker micrOTOF-Q II mass spectrometer was used for ESI-MS analysis (positive mode). Infrared spectra were obtained using a Perkin Elmer Spectrum One Fourier Transform infrared spectrometer with a universal ATR sampling accessory. Peptide purification was performed using a Waters 600E or Dionex Ultimate U3000 system using a Waters XTerra.(R). column (C18, 300 mm .x. 19 mm; 10 mum), or Phenomenex Gemini C18, 250 mm .x. 10 mm; 5 mum column. Gradient systems were adjusted according to the elution profiles and peak profiles obtained from the analytical RP-HPLC chromatograms. Fractions were collected, analysed by either RP-HPLC or ESI-MS, pooled and lyophilised three times from 10 mM aq HCl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Fmoc SPPS was performed on a Liberty Microwave Peptide Synthesiser (CEM Corporation, Mathews, NC) using the Fmoc/tBu strategy as previously described35 or manually starting from PAL-PEG polystyrene resin (0.21 mmol/g). For manual synthesis the following steps were undertaken: (a) Fmoc deprotection with 20percent piperidine for 5 min, then 15 min, washing with DMF 5.x.; (b) coupling of the Fmoc amino acid (5 equiv) in the presence of HBTU in DMF (4.9 equiv) and iPr2NEt (10 equiv) for 1 h and washing with DMF 5.x.. For coupling of Fmoc-Pra (1.5 equiv) and Fmoc-N3Ala (1.5 equiv), 1.45 equiv of HBTU and 4.5 equiv of iPr2NEt were used. The progress of the acylation step was monitored by the Kaiser test. A minimum amount of DMF was used for dissolution of the Fmoc amino acid. The resulting peptides were cleaved from the resin with simultaneous side chain protecting group removal by treatment with either TFA/iPr3SiH/DODT/H2O (v/v/v/v; 94/1/2.5/2.5), or with TFA/iPr3SiH/H2O (v/v/v; 95/2.5/2.5) for 2 h at room temperature. Crude peptides were precipitated and triturated with cold diethyl ether, isolated (centrifugation), dissolved in 20percent acetonitrile (aq) containing 0.1percent TFA and lyophilized. Analytical RP-HPLC was performed using a Dionex P680 (flow rate of 1 mL/min), or Dionex Ultimate U3000 system (flow rate of 0.5 mL/min or 0.2 mL/min) using Waters XTerra.(R). column (MS C18, 150 mm .x. 4.6 mm; 5 mum) or, Phenomenex Aqua column (C18, 250 mm .x. 4.6 mm; 5mu), or Phenomenex, Gemini column (C18, 50 mm .x. 2.0 mm, 5mu), using gradient systems as indicated in the Supplementary data. The solvent system used was A (0.1percent TFA in H2O) and B (0.1percent TFA in acetonitrile) with detection at 210 nm, 254 nm, and 280 nm****. The ratio of products was determined by integration of spectra recorded at 210 nm. Peptide masses were confirmed by an inline Thermo Finnegan MSQ mass spectrometer using ESI in the positive mode. When appropriate, a Bruker micrOTOF-Q II mass spectrometer was used for ESI-MS analysis (positive mode). Infrared spectra were obtained using a Perkin Elmer Spectrum One Fourier Transform infrared spectrometer with a universal ATR sampling accessory. Peptide purification was performed using a Waters 600E or Dionex Ultimate U3000 system using a Waters XTerra.(R). column (C18, 300 mm .x. 19 mm; 10 mum), or Phenomenex Gemini C18, 250 mm .x. 10 mm; 5 mum column. Gradient systems were adjusted according to the elution profiles and peak profiles obtained from the analytical RP-HPLC chromatograms. Fractions were collected, analysed by either RP-HPLC or ESI-MS, pooled and lyophilised three times from 10 mM aq HCl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | General procedure: Solid-phase peptide synthesis was carried out on Fmoc-cappedpolystyrene rink amide MBHA resin (100-200 mesh, 0.05-0.15 mmol scale). The following amino acidderivatives suitable for Fmoc SPPS were used: Fmoc-Cys(Trt)-OH, Fmoc-Gly-OH, Fmoc-Glu(tBu)-OH,Fmoc-Trp(Boc)-OH, Fmoc-Ala-OH, Fmoc-Tyr(tBu)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Pro-OH, Fmoc-Thr(tBu)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Phe-OH, Fmoc-Val-OH, Fmoc-aPhe-OH, Fmoc-aVal-OH,Fmoc-aTyr(tBu)-OH, Fmoc-(N-Me)-Phe-OH, Fmoc-D-Ser(TBS)-OH, Fmoc-D-hSer(TBS)-OH, Boc-Gly-OH. Dry resin was washed with DMF 3x and allowed to swell in DMF for 2 h prior to use. Allreactions were carried out using gentle agitation. Fmoc deprotection steps were carried out by treating theresin with a solution of 20percent piperidine/DMF (15 min x 2). Coupling of Fmoc-protected amino acids aswell as (N2-Boc)-hydrazino acids was effected using 5 equiv. HATU (0.5 M in DMF), 10 equiv. DIEA(1.0 M in DMF), and 5 equiv. of the carboxylic acid in DMF at 50 oC (1 h). Coupling of residues Nterminalto the hydrazino acids was carried out with 30 equiv. collidine and 10 equiv. of pre-formed Fmocamino acid chlorides (or 10 equiv. of Fmoc amino acids with 3.3 equiv. triphosgene) in THF at rt (1 h x2).3 After each reaction the resin was washed with DMF 2x, DCM 1x, then DMF 1x. Peptides undergoingMitsunobu reactions were capped with Boc-Gly-OH, washed with DCM 3x, and treated with 5 equiv.TBAF in THF for 3 h at rt. After the reaction the resin was washed with DCM 3x and then treated with 5equiv. triphenylphosphine in THF followed by 5 equiv. of DIAD, then strirred overnight at rt. Peptideswere cleaved from the resin by incubating with gentle stirring in 2 mL of 95:5 TFA:H2O at rt for 2 h. Thecleavage mixture was filtered and the resin was rinsed with an additional 1 mL of cleavage solution. Thefiltrate was treated with 8 mL of cold Et2O to induce precipitation. The mixture was centrifuged and thesupernatant was removed. The remaining solid was washed 2 more times with Et2O and dried undervacuum. Cysteine-containing peptides were purified, lyophilized, dissolved in 10mM phosphate buffer(pH 8.9, 5percent v/v DMSO), stirred until analytical HPLC and MS showed complete conversion to the cyclicdisulfide (1-2 d), and then repurified. Peptides were analyzed and purified on C12 RP-HPLC columns(preparative: 4mu, 90A, 250 x 21.2 mm; analytical: 4mu, 90A, 150 x 4.6 mm) using linear gradients ofMeCN/H2O (with 0.1percent formic acid), then lyophilized to afford white powders. All peptides werecharacterized by LCMS (ESI), HRMS (ESI-TOF), and 1H NMR. Analytical HPLC samples for all purifiedpeptides were prepared as 1 mM in H2O containing 20 mM phosphate buffer at pH 7.0. Linear gradientsof MeCN in H2O (0.1percent formic acid) were run over 20 minutes and spectra are provided for lambda = 220 nm. |
Tags: 71989-35-0 synthesis path| 71989-35-0 SDS| 71989-35-0 COA| 71989-35-0 purity| 71989-35-0 application| 71989-35-0 NMR| 71989-35-0 COA| 71989-35-0 structure
[ 117106-20-4 ]
(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(tert-butoxy)butanoic acid
Similarity: 0.95
[ 1217603-41-2 ]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-methylbutanoic acid
Similarity: 0.95
[ 884880-39-1 ]
(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-methylbutanoic acid
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Precautionary Statements-General | |
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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 |
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