Improved solid-phase peptide synthesis method utilizing α-azide-protected amino acids

被引：182

作者：

Lundquist, JT ^{[1
]}

Pelletier, JC ^{[1
]}

机构：

[1] Wyeth Ayerst Res, Div Discovery Chem, Radnor, PA 19087 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol0155485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Pure alpha -azido acids were prepared using an efficient diazo transfer method followed by buffered workup, These building blocks were used to prepare small peptides on Wang resin by two approaches, Peptides prone to diketopiperazine formation were prepared in good yields by coupling acids to resin bound iminophosphoranes during Fmoc-Wang synthesis, The iminophosphoranes can also be hydrolyzed under neutral conditions to provide unprotected amines ready for further coupling.

引用

页码：781 / 783

页数：3

共 50 条

[31] Solid-phase synthesis of novel peptide nucleic acids
Lowe, G
Vilaivan, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 555 - 560
[32] Solid-phase synthesis of peptide ribonucleic acids (PRNA)
Sato, H
Hashimoto, Y
Wada, T
Inoue, Y
TETRAHEDRON, 2003, 59 (40) : 7871 - 7878
[33] Synthesis of all nineteen appropriately protected chiral α-hydroxy acid equivalents of the α-amino acids for Boc solid-phase depsi-peptide synthesis
Deechongkit, S
You, SL
Kelly, JW
ORGANIC LETTERS, 2004, 6 (04) : 497 - 500
[34] IMPROVED SOLID-PHASE METHOD FOR PEPTIDE-SYNTHESIS - SYNTHESES OF OXYTOCIN AND VASOPRESSIN
不详
SCIENTIA SINICA, 1975, 18 (02): : 233 - 241
[35] RACEMIZATION OF ACTIVATED, URETHANE-PROTECTED AMINO-ACIDS BY PARA-DIMETHYLAMINOPYRIDINE - SIGNIFICANCE IN SOLID-PHASE PEPTIDE-SYNTHESIS
ATHERTON, E
BENOITON, NL
BROWN, E
SHEPPARD, RC
WILLIAMS, BJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) : 336 - 337
[36] GLYCOLAMIDIC ESTER GROUP AS LABILE LINKAGE IN SOLID-PHASE PEPTIDE-SYNTHESIS - USE WITH FMOC-PROTECTED AMINO-ACIDS
BALEUX, F
CALAS, B
MERY, J
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1986, 28 (01): : 22 - 28
[37] AMINO-LACTAM PEPTIDE SYNTHESIS USING FMOC- PROTECTED CYCLIC SULFAMIDATES ON SOLID-PHASE
Boulard, N.
Jamieson, A.
Beauregard, K.
Bodas, M.
Ong, H.
Quiniou, C.
Chemtob, S.
Lubell, W. D.
BIOPOLYMERS, 2009, 92 (04) : 330 - 330
[38] Fullerene-derivatized amino acids: Synthesis, characterization, antioxidant properties, and solid-phase peptide synthesis
Yang, Jianzhong
Alemany, Lawrence B.
Driver, Jonathan
Hartgerink, Jeffrey D.
Barron, Andrew R.
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (09) : 2530 - 2545
[39] Synthesis of suitably protected γ-hydroxyvaline for use in fmoc solid-phase peptide synthesis
Cudic, M.
Mari, F.
Fields, G. B.
BIOPOLYMERS, 2007, 88 (04) : 574 - 574
[40] Synthesis of orthogonally protected thioamide dipeptides for use in solid-phase peptide synthesis
Manzor, Kim
Kelleher, Fintan
TETRAHEDRON LETTERS, 2016, 57 (47) : 5237 - 5239

← 1 2 3 4 5 →