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

[1] Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids
Baird, EE
Dervan, PB
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) : 6141 - 6146
[2] Solid-phase synthesis of α,α-difluorinated β-amino acids by Reformatsky reaction
Nefzi, A
Vidal, A
Houghten, RA
BIOPOLYMERS, 2003, 71 (03) : 353 - 353
[3] Amino monothio acids in solid-phase synthesis of peptide thioamides
HoegJensen, T
Spatola, AF
Holm, A
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1996, 47 (03): : 190 - 200
[4] Solid phase peptide synthesis using nanoparticulate amino acids in water
Hojo, K.
Ichikawa, H.
Maeda, M.
Fukumori, Y.
Kawasaki, K.
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 242 - 242
[5] N-Fmoc-dehydroalanine:: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids
Burkett, BA
Chai, CLL
TETRAHEDRON LETTERS, 2000, 41 (34) : 6661 - 6664
[6] Solid-phase peptide synthesis using nanoparticulate amino acids in water
Hojo, Keiko
Ichikawa, Hideki
Iviaeda, Mitsuko
Kida, Shinya
Fukumori, Yoshinobu
Kawasaki, Koichi
JOURNAL OF PEPTIDE SCIENCE, 2007, 13 (07) : 493 - 497
[7] Solid phase synthesis of peptides containing backbone-fluorinated amino acids
Hunter, Luke
Butler, Sharon
Ludbrook, Steven B.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) : 8911 - 8918
[8] Solid-phase synthesis of α-amino acids by radical addition to a dehydroalanine derivative
Yim, AM
Vidal, Y
Viallefont, P
Martinez, J
TETRAHEDRON LETTERS, 1999, 40 (24) : 4535 - 4538
[9] Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids
Wurtz, NR
Turner, JM
Baird, EE
Dervan, PB
ORGANIC LETTERS, 2001, 3 (08) : 1201 - 1203
[10] Solid-phase synthesis of phosphonopeptides from P(III) amino acids
Hammer, RP
Fernandez, MD
Fan, H
Kappel, JC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 259 - ORGN

← 1 2 3 4 5 →