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
收藏
页码：6287 / 6290
页数：4
相关论文
共 22 条
  • [1] ASPARAGINE AS A MASKED DEHYDROALANINE RESIDUE IN SOLID-PHASE PEPTIDE-SYNTHESIS
    BLETTNER, C
    BRADLEY, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (03) : 467 - 470
  • [2] Combinatorial organic synthesis using Parke-Davis's DIVERSOMER method
    DeWitt, SH
    Czarnik, AW
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) : 114 - 122
  • [3] DUNNILL PM, 1965, PHYTOCHEMISTRY, V4, P935
  • [4] QUISQUALAMINE, A NOVEL GAMMA-AMINOBUTYRIC ACID (GABA)-RELATED DEPRESSANT AMINO-ACID
    EVANS, RH
    FRANCIS, AA
    HUNT, K
    MARTIN, MR
    WATKINS, JC
    [J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1978, 30 (06) : 364 - 367
  • [5] Organic chemistry on solid supports
    Fruchtel, JS
    Jung, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01): : 17 - 42
  • [6] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES
    GALLOP, MA
    BARRETT, RW
    DOWER, WJ
    FODOR, SPA
    GORDON, EM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) : 1233 - 1251
  • [7] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS
    GORDON, EM
    BARRETT, RW
    DOWER, WJ
    FODOR, SPA
    GALLOP, MA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) : 1385 - 1401
  • [8] Tandem UPS: Sequential mono- and dialkylation of resin-bound glycine via automated synthesis
    Griffith, DL
    ODonnell, MJ
    Pottorf, RS
    Scott, WL
    Porco, JA
    [J]. TETRAHEDRON LETTERS, 1997, 38 (51) : 8821 - 8824
  • [9] Solid-phase organic reactions: A review of the recent literature
    Hermkens, PHH
    Ottenheijm, HCJ
    Rees, D
    [J]. TETRAHEDRON, 1996, 52 (13) : 4527 - 4554
  • [10] Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96.
    Hermkens, PHH
    Ottenheijm, HCJ
    Rees, DC
    [J]. TETRAHEDRON, 1997, 53 (16) : 5643 - 5678
123