Rapid solid phase synthesis of α-amino acids

被引：20

作者：

Barbaste, M ^{[1
]}

Rolland-Fulcrand, V ^{[1
]}

Roumestant, ML ^{[1
]}

Viallefont, P ^{[1
]}

Martinez, J ^{[1
]}

机构：

[1] Univ Montpellier 1 & 2, Lab Aminoacides Peptides & Prot, CNRS, UMR 5810, F-34095 Montpellier 5, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(98)01328-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A solid phase synthetic method for amino acids is developed. The N-acetyl-dehydroalanine is quantitatively bound to Wang resin by the Mitsunobu method. Then a Michael addition is achieved on the double bond with different nucleophiles. Non proteinic N-acetyl-alpha-amino acids are obtained after cleavage from the resin by mild acid treatment (Scheme 1). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：6287 / 6290

页数：4

共 50 条

[31] Solid-Phase Synthesis of Peptide Libraries Combining α-Amino Acids with Inorganic and Organic Chromophores
Heinze, Katja
Hempel, Klaus
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (06) : 1346 - 1358
[32] Masked side-chain aldehyde amino acids for solid-phase synthesis and ligation
Spetzler, JC
Hoeg-Jensen, T
TETRAHEDRON LETTERS, 2002, 43 (12) : 2303 - 2306
[33] Solution and solid phase combinatorial synthesis of peptidomimetic library containing diversified α-methylated amino acids
Kim, SW
Shin, YS
Ro, SG
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (13) : 1665 - 1668
[34] Progress towards the development of novel solid phase peptide synthesis using phosphorylated amino acids
White, Dawanna S.
Berkman, Clifford E.
Choy, Cindy J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[35] Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines
Małgorzata Koprowska-Ratajska
Alicja Kluczyk
Piotr Stefanowicz
Hubert Bartosz-Bechowski
Zbigniew Szewczuk
Amino Acids, 2009, 36
[36] 4-METHOXYBENZYLOXYCARBONYL AMINO-ACIDS IN SOLID-PHASE PEPTIDE-SYNTHESIS
WANG, SS
CHEN, ST
WANG, KT
MERRIFIELD, RB
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1987, 30 (05): : 662 - 667
[37] Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines
Koprowska-Ratajska, Malgorzata
Kluczyk, Alicja
Stefanowicz, Piotr
Bartosz-Bechowski, Hubert
Szewczuk, Zbigniew
AMINO ACIDS, 2009, 36 (02) : 309 - 315
[38] Synthesis of diastereoisomeric modified amino acids derived from -lipoic acid for use in solid phase peptide synthesis
Rentier, C.
Nuti, F.
Pacini, G.
Rovero, P.
Selmi, C.
Papini, A. M.
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S187 - S187
[39] Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis
Jaramillo, D
Liu, Q
Aldrich-Wright, J
Tor, Y
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23): : 8151 - 8153
[40] 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

← 1 2 3 4 5 →