[ CAS No. 71989-23-6 ] {[proInfo.proName]}

Name: 71989-23-6|Fmoc-Ile-OH|98%
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Quality Control of [ 71989-23-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 71989-23-6 ]

SDS Specification

Alternatived Products of [ 71989-23-6 ]

Product Details of [ 71989-23-6 ]

CAS No. :	71989-23-6	MDL No. :	MFCD00037125
Formula :	C₂₁H₂₃NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QXVFEIPAZSXRGM-DJJJIMSYSA-N
M.W :	353.41	Pubchem ID :	2724629
Synonyms :	Fmoc-L-isoleucine

Calculated chemistry of [ 71989-23-6 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.33
Num. rotatable bonds :	8
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	99.59
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.54
Log Po/w (XLOGP3) :	4.38
Log Po/w (WLOGP) :	4.02
Log Po/w (MLOGP) :	3.0
Log Po/w (SILICOS-IT) :	3.55
Consensus Log Po/w :	3.5

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.6
Solubility :	0.00879 mg/ml ; 0.0000249 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.68
Solubility :	0.000731 mg/ml ; 0.00000207 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.71
Solubility :	0.000689 mg/ml ; 0.00000195 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.05

Safety of [ 71989-23-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 71989-23-6 ]

* 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.

Upstream synthesis route of [ 71989-23-6 ]
Downstream synthetic route of [ 71989-23-6 ]

[ 71989-23-6 ] Synthesis Path-Upstream 1~12

1
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 36077-41-5 ]

Reference： [1] Marine Drugs, 2013, vol. 11, # 12, p. 4834 - 4857

2
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 1403834-74-1 ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 50-56-6 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 3, p. 616 - 619

3
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 103213-32-7 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 50-56-6 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 19, p. 6074 - 6078

4
[ 68858-20-8 ]
[ 71989-31-6 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 109425-51-6 ]
[ 4474-91-3 ]

Reference： [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 35, p. 5427 - 5434

5
[ 73-32-5 ]
[ 71989-23-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In acetonitrile at 20℃; for 2 h;	General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 16, p. 1600 - 1603

6
[ 73-32-5 ]
[ 82911-69-1 ]
[ 71989-23-6 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 283 - 287[2] Bioorganicheskaya Khimiya, 1999, vol. 25, # 5, p. 323 - 328
[3] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 2980 - 2983

7
[ 73-32-5 ]
[ 28920-43-6 ]
[ 71989-23-6 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 24, p. 18751 - 18760
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515

8
[ 73-32-5 ]
[ 88744-04-1 ]
[ 71989-23-6 ]

Reference： [1] Synthesis, 1986, # 4, p. 303 - 305

9
[ 73-32-5 ]
[ 102774-86-7 ]
[ 71989-23-6 ]

Reference： [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098

10
[ 28920-43-6 ]
[ 17694-98-3 ]
[ 71989-23-6 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582

11
[ 71989-23-6 ]
[ 133565-46-5 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 87, p. 46947 - 46950
[2] Tetrahedron Letters, 1991, vol. 32, # 7, p. 923 - 926
[3] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[4] Synlett, 2010, # 5, p. 715 - 720

12
[ 71989-23-6 ]
[ 138775-22-1 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 44, p. 6109 - 6112

[ 71989-23-6 ] Synthesis Path-Downstream 1~88

1
[ 29022-11-5 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 77128-73-5 ]
Fmoc-D-Asp(t-Bu)-OH, Hpa-OSu, Fmoc-MeAsp(t-Bu)-OH, Fmoc-Nle [ No CAS ]
(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-({(2S,3S)-2-[(S)-2-(2-{(S)-2-[2-(4-hydroxy-phenyl)-acetylamino]-hexanoylamino}-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-3-methyl-pentanoyl}-methyl-amino)-N-methyl-succinamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 4302 - 4307

2
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 198561-07-8 ]
Ac-Ile-Asp-Phe-Gly-OH [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 2469 - 2472

3
[ 35661-39-3 ]
[ 13734-38-8 ]
[ 71989-23-6 ]
[ 187089-29-8 ]
Fmoc-Ser(t-Bu)-Ser(t-Bu)-NH-Rink-Amide resin [ No CAS ]
Fmoc-Asn-OH [ No CAS ]
[ 915103-91-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 3587 - 3597

4
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₇₅H₂₁₄N₂₁O₂₄PolS₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633

5
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₃₁H₁₇₆N₁₉O₂₂PolS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633

6
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 118358-38-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₈₅H₂₂₄N₂₁O₃₃PolS₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633

7
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 96402-49-2 ]
[ 118358-38-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₄₁H₁₈₆N₁₉O₃₁PolS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633

8
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1160810-26-3 ]

Reference： [1]Heterocycles,2009,vol. 79,p. 925 - 933

9
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-30-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 446 - 457

10
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-28-8 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 446 - 457

11
Fmoc-His(1-Bzl)-OH [ No CAS ]
[ 71989-23-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
[ 1213772-59-8 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 86 - 95

12
Fmoc-His(1-Bzl)-OH [ No CAS ]
[ 71989-23-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 1213773-56-8 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 86 - 95

13
Fmoc-His(1-Bzl)-OH [ No CAS ]
[ 71989-23-6 ]
[ 86123-10-6 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 1213772-92-9 ]

Reference： [1]ChemMedChem,2010,vol. 5,p. 86 - 95

14
Fmoc-Leu-Wang resin [ No CAS ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
[ 1198076-80-0 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 976 - 979

15
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-16-7 ]
[ 91000-69-0 ]
[ 198561-07-8 ]
C₅₇H₉₃N₁₇O₂₂ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5604 - 5607

16
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
H-(propargylglycyl)-QGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA-NH₂ [ No CAS ]

Reference： [1]Journal of Peptide Science,2011,vol. 17,p. 270 - 280

17
[ 258332-56-8 ]
C₂₉H₃₀NO₄Pol [ No CAS ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 105047-45-8 ]
[ 198561-07-8 ]
C₄₄H₇₀N₈O₁₀ [ No CAS ]

Reference： [1]ChemMedChem,2013,vol. 8,p. 75 - 81

18
[ 35661-39-3 ]
C₂₄H₂₉NO₆ [ No CAS ]
[ 122889-11-6 ]
[ 71989-23-6 ]
(3S,7S,10S,13S)-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-13-(benzyloxymethyl)-10-sec-butyl-7-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: The peptides were synthesized on an activated [44] 2-chlorotrityl chloride resin (1 g) which had been swelled in dry DCM for 30 min. The first Fmoc amino acid (4 equiv) was coupled to the resin manually using dry DCM (10 mL) and DIPEA (6 equiv) for 2 h under a N2 atmosphere. Resin substitution was then determined using the Fmoc UV assay. On 0.1 mM scale subsequent amino acids were also coupled manually using amino acid (0.20 mM, 2.5 mL), DIPEA (1 mM, 1.0 mL) and HBTU (0.50 mM, 1.0 mL) in DMF. The Fmoc group of amino acid was removed using 20percent piperidine?DMF (3 × 10 mL) for 30 min and the next amino acid and sugar amino acid 1a/b were coupled on resin using the same condition. The excess reagents were washed with DMF (2 × 7 mL) and DCM (2 × 7 mL). Cleavage from resin was performed manually, using a cleavage mixture of TFA?DCM [5:95percent (v/v), 3 × 10 mL] for 30 min. The crude compound was then purified using semi-preparative HPLC. All compounds were obtained in good yields.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 144 - 154

19
[ 35661-39-3 ]
C₂₂H₃₁NO₈ [ No CAS ]
[ 122889-11-6 ]
[ 71989-23-6 ]
(2S)-2-((2S,3S)-2-((2S)-2-((3S)-3-amino-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propanamido)propanamido)-3-methylpentanamido)-3-(benzyloxy)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: The peptides were synthesized on an activated [44] 2-chlorotrityl chloride resin (1 g) which had been swelled in dry DCM for 30 min. The first Fmoc amino acid (4 equiv) was coupled to the resin manually using dry DCM (10 mL) and DIPEA (6 equiv) for 2 h under a N2 atmosphere. Resin substitution was then determined using the Fmoc UV assay. On 0.1 mM scale subsequent amino acids were also coupled manually using amino acid (0.20 mM, 2.5 mL), DIPEA (1 mM, 1.0 mL) and HBTU (0.50 mM, 1.0 mL) in DMF. The Fmoc group of amino acid was removed using 20percent piperidine?DMF (3 × 10 mL) for 30 min and the next amino acid and sugar amino acid 1a/b were coupled on resin using the same condition. The excess reagents were washed with DMF (2 × 7 mL) and DCM (2 × 7 mL). Cleavage from resin was performed manually, using a cleavage mixture of TFA?DCM [5:95percent (v/v), 3 × 10 mL] for 30 min. The crude compound was then purified using semi-preparative HPLC. All compounds were obtained in good yields.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 60,p. 144 - 154

20
Fmoc-Asp(otBu)-Wang resin [ No CAS ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 120791-76-6 ]
[ 198561-07-8 ]
[ 684270-46-0 ]
C₁₃₅H₁₈₂N₁₈O₂₃S₃ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7753 - 7762

21
Fmoc-Gly-Wang resin [ No CAS ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 13734-38-8 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 86060-81-3 ]
Fmoc-Ala-Thr(Ψ^Me,Mepro)-OH [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 268209-75-2 ]
(Boc-Ser(tBu))-Lys(Boc)-Glu(OtBu)-Pro-Leu-Arg(pbf)-Pro-Arg(pbf)-(S-(acetylaminomethyl)Cys)-Arg(pbf)-Pro-Ile-(O-(2-(isopropyl)phenyl)Asp)-Ala-(N,O-isopropylidene-Thr)-Leu-Ala-Val-Glu(OtBu)-Lys(Boc)-Glu(OtBu)-Gly-OH [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 8450 - 8458

22
Fmoc-Gly-Wang resin [ No CAS ]
[ 957780-52-8 ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-39-3 ]
[ 13734-38-8 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 86060-81-3 ]
Fmoc-Ala-Thr(Ψ^Me,Mepro)-OH [ No CAS ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 268209-75-2 ]
(Boc-Ser(tBu))-Lys(Boc)-Glu(OtBu)-Pro-Leu-Arg(pbf)-(S-(acetylaminomethyl)Cys)-Arg(pbf)-Pro-Ile-(O-(2-(isopropyl)phenyl)Asp)-Ala-(N,O-isopropylidene-Thr)-Leu-Ala-Val-Glu(OtBu)-Lys(Boc)-Glu(OtBu)-Gly-(S-(acetylaminomethyl)Cys)-Pro-Val-(S-(acetylaminomethyl)Cys)-Ile-(N,O-isopropylidene-Thr)-Val-(O-(2-(isopropyl)phenyl)Asp)-Thr(tBu)-Thr(tBu)-Ile-(S-(acetylaminomethyl)Cys)-Ala-Gly-OH [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 8450 - 8458

23
Fmoc-Gly-Wang resin [ No CAS ]
[ 957780-52-8 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 13734-38-8 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 86060-81-3 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 268209-75-2 ]
Ser(Boc)-Arg(pbf)-Glu(OtBu)-Pro-Leu-Arg(pbf)-Pro-Trp(Boc)-(S-(acetylaminomethyl)Cys)-His(Trt)-Pro-Ile-Asn(Trt)-Ala-Ile-Leu-Ala-Val-Glu(OtBu)-Lys(Boc)-Glu(OtBu)-Gly-(S-(acetylaminomethyl)Cys)-Pro-Val-(S-(acetylaminomethyl)Cys)-Ile-(N,O-isopropylidene-Thr)-Val-(O-(2-(isopropyl)phenyl)Asp)-Thr(tBu)-Thr(tBu)-Ile-(S-(acetylaminomethyl)Cys)-Ala-Gly-OH [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 8450 - 8458

24
[ 71989-23-6 ]
[ 24629-25-2 ]
C₂₇H₃₆N₂O₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 632 - 635

25
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGA-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314

26
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGF-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314

27
Fmoc-alanine-Wang-resin [ No CAS ]
[ 122889-11-6 ]
[ 108-24-7 ]
[ 71989-23-6 ]
N-acetyl-L-isoleucyl-L-(OBn)seryl-L-alanine [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 22431 - 22448

28
Fmoc-Leu-Wang resin [ No CAS ]
[ 214750-72-8 ]
[ 258332-56-8 ]
[ 71989-31-6 ]
[ 71989-23-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
H-propargyl-Gly-N-Me-Arg-Lys-Pro-N-homo-Tyr-Ile-Leu-OH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The solid phase peptide synthesis (SPPS) was performed using a microwave assisted protocol (Discover microwave oven, CEMCorp.) starting from Fmoc-Leu-Wang resin. The reactions were carried out in a silanized glass tube loosely sealed with a silicon septum. Remark: the development of overpressure was avoided by using DMF as the solvent and intermittent cooling in an ethanol-ice bath. The amino acids were incorporated as their commercially available derivatives in the following order: Fmoc-Ile-OH, Fmoc-N-homo-Tyr(tBu)-OH (synthesized according to ref. 18), Fmoc-Pro-OH, Fmoc-Arg(Pbf)-OH, Fmoc-N-Me-Arg(Mtr)-OH and Fmoc-propargyl-Gly-OH. Elongation of the peptide chain was performedby repetitive cycles of Fmoc deprotection and subsequent couplings of the amino acid. Fmoc deprotection was performed by treating the resin with 25% piperidine in DMF (microwave irradiation: 7 5 s, 100 W), followed by washings with DMF (5). In between each irradiation step, cooling of the reaction mixture to a temperature of 10 C was achieved by sufficient agitation in an ethanol-ice bath. Peptide couplings of Fmoc-Ile-OH, Fmoc-Arg(Pbf)-OH and Fmoc-N-Me-Arg(Mtr)-OH were performed employing 5 equiv of each Fmoc-AA/PyBOP/DIPEA and 7.5 equiv 1-hydroxybenzotriazole (HOBt), dissolved in a minimum amount of DMF (irradiation: 20 10 s, 50W and intermittent cooling). Fmoc-N-homo-Tyr(tBu)-OH (3 equiv) was coupled with 3 equiv PyBOP/DIPEA and 4.5 equiv HOBt in DMF. Fmoc-Pro-OH (5 equiv)and Fmoc-propargyl-Gly-OH (5 equiv) were subjected to a double coupling with HATU (5 equiv) and DIPEA (10 equiv) in DMF. After the last acylation step, the N-terminal Fmoc-residue was deprotected, the resin was 10 rinsed with CH2Cl2 and dried in vacuo. The cleavage from the resin was performed using a mixture of trifluoroacetic acid (TFA)/phenol/H2O/triisopropylsilane (TIS) 88:6:4:2 for 4 h, followed by a filtration of the resin. After evaporation of the solvent in vacuo and precipitation in t-butylmethylether, the crude peptides were purified using preparative RP-HPLC (Agilent 1100 preparative series, column Zorbax Eclipse XDB-C8, 21.2 mm, 150 mm, 5 lm particles, flow rate 10 mL/min) with the solvent system 3-35% acetonitrile in water (0.1% HCO2H) in a linear gradient over 18.0 min, tR: 10.5 min. After the separation, the peptide was lyophilized and peptide purity and identity were assessed by analytical HPLC (Agilent 1100 analytical series, equipped with QuatPump and VWD detector; column ZorbaxEclipse XDB-C8 analytical column, 4.6 mm, 150 mm, 5 lm, flow rate 0.5 mL/min) coupled to a Bruker Esquire 2000 mass detector equipped with an ESI-trap. ESI-TOF high mass accuracy and resolution experiments were performed on a BRUKER maXis MS (BrukerDaltonics, Bremen) in the laboratories of the Chair of OrganicChemistry (Prof. Dr. Rik Tykwinski), Department of Pharmacy and Chemistry, Friedrich-Alexander University of Erlangen Nuremberg. Purity: solvent system 1: 10-55% methanol in water (0.1% HCO2H)in a linear gradient over 18 min, tR = 14.6 min (>99 %); solvent system 2: 3-40% acetonitrile in water (0.1% HCO2H) in a linear gradient over 26 min, tR = 15.9 min (>99%). ESI-MS: m/z calcd:940.6, found: 940.6 [M+H]+; HR-ESI-TOF: [M+H]+ calcd forC45H74N13O9: 940.5732, found: 940.5724.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4026 - 4033

29
[ 29022-11-5 ]
[ 35661-60-0 ]
C₂₂H₂₀NOPolS [ No CAS ]
[ 112883-29-1 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
(1-naphthylalanine)SCIDTIPKSRCTAFQCKHSMKYRLSFCRKTCGTC; disulfide linked (C3→35, C12→28, C17→32) [ No CAS ]