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

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines
Alper, PB
Hung, SC
Wong, CH
[J]. TETRAHEDRON LETTERS, 1996, 37 (34) : 6029 - 6032
[2] Synthesis and effects of active fragments of angiotensin II
Ardaillou, R
Chansel, D
[J]. KIDNEY INTERNATIONAL, 1997, 52 (06) : 1458 - 1468
[3] Synthesis of a tripeptide derivative containing the Phe-Arg hydroxyethylene dipeptide isostere
Brewer, M
Rich, DH
[J]. ORGANIC LETTERS, 2001, 3 (06) : 945 - 948
[4] TRIFLUOROMETHANESULFONYL AZIDE - ITS REACTION WITH ALKYL AMINES TO FORM ALKYL AZIDES
CAVENDER, CJ
SHINER, VJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) : 3567 - &
[5] An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles
Demko, ZP
Sharpless, KB
[J]. ORGANIC LETTERS, 2001, 3 (25) : 4091 - 4094
[6] NEW SYNTHETIC TRICKS - TRIPHENYLPHOSPHINE-MEDIATED AMIDE FORMATION FROM CARBOXYLIC-ACIDS AND AZIDES
GARCIA, J
URPI, F
VILARRASA, J
[J]. TETRAHEDRON LETTERS, 1984, 25 (42) : 4841 - 4844
[7] POTENT, STRUCTURALLY CONSTRAINED AGONISTS AND COMPETITIVE ANTAGONISTS OF CORTICOTROPIN-RELEASING FACTOR
GULYAS, J
RIVIER, C
PERRIN, M
KOERBER, SC
SUTTON, S
CORRIGAN, A
LAHRICHI, SL
CRAIG, AG
VALE, W
RIVIER, J
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (23) : 10575 - 10579
[8] COLOR TEST FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN SOLID-PHASE SYNTHESIS OF PEPTIDES
KAISER, E
COLESCOT.RL
BOSSINGE.CD
COOK, PI
[J]. ANALYTICAL BIOCHEMISTRY, 1970, 34 (02) : 595 - &
[9] COMPLETE AMINO-ACID SEQUENCE OF HUMAN PARATHYROID-HORMONE
KEUTMANN, HT
SAUER, MM
HENDY, GN
ORIORDAN, JLH
POTTS, JT
[J]. BIOCHEMISTRY, 1978, 17 (26) : 5723 - 5729
[10] Synthesis of a novel β-turn mimetic and its incorporation in Leu-enkephalin
Kreye, P
Kihlberg, J
[J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 6113 - 6116

← 1 2 3 →