A convenient synthesis of azido peptides by post-assembly diazo transfer on the solid phase applicable to large peptides

被引：33

作者：

Rijkers, DTS ^{[1
]}

van Vugt, HHR ^{[1
]}

Jacobs, HJF ^{[1
]}

Liskamp, RMJ ^{[1
]}

机构：

[1] Univ Utrecht, Fac Pharmaceut Sci, Utrecht Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期

关键词：

azides; azido peptides; diazo transfers; solid phase synthesis;

D O I：

10.1016/S0040-4039(02)00629-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the conversion of solid phase bound peptide amines into azides by a diazo transfer using triflyl azide in the presence of divalent copper ions is described. alpha-Azido acids and azido peptides-up to 30 amino acids in length-are obtained in good yields and high purities after cleavage from the solid support. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3657 / 3660

页数：4

共 26 条

[11] Improved solid-phase peptide synthesis method utilizing α-azide-protected amino acids [J].

Lundquist, JT ;

Pelletier, JC .

ORGANIC LETTERS, 2001, 3 (05) :781-783

[12] Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction [J].

Malkinson, JP ;

Falconer, RA ;

Toth, I .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5249-5252

[13] One-pot synthesis of glycosyl amides from glycosyl azides using a modified Staudinger reaction [J].

Maunier, V ;

Boullanger, P ;

Lafont, D .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (02) :231-235

[14] Azido acids in a novel method of solid-phase peptide synthesis. [J].

Meldal, M ;

Juliano, MA ;

Jansson, AM .

TETRAHEDRON LETTERS, 1997, 38 (14) :2531-2534

[15]

Mizuno M, 1999, SYNTHESIS-STUTTGART, P162

[16] Staudinger ligation: A peptide from a thioester and azide [J].

Nilsson, BL ;

Kiessling, LL ;

Raines, RT .

ORGANIC LETTERS, 2000, 2 (13) :1939-1941

[17] High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide [J].

Nilsson, BL ;

Kiessling, LL ;

Raines, RT .

ORGANIC LETTERS, 2001, 3 (01) :9-12

[18] Cell surface engineering by a modified Staudinger reaction [J].

Saxon, E ;

Bertozzi, CR .

SCIENCE, 2000, 287 (5460) :2007-2010

[19] A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds [J].

Saxon, E ;

Armstrong, JI ;

Bertozzi, CR .

ORGANIC LETTERS, 2000, 2 (14) :2141-2143

[20]

Tornoe CW, 2000, J PEPT SCI, V6, P594, DOI 10.1002/1099-1387(200012)6:12<594::AID-PSC276>3.0.CO

← 1 2 3 →