A novel and mild solid phase hydroperoxydeamination reaction

被引：5

作者：

Bonnet, D

Rommens, C

Gras-Masse, H

Melnyk, O

机构：

[1] Inst Pasteur, Inst Biol, F-59021 Lille, France

[2] Univ Lille 2, F-59021 Lille, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 41期

关键词：

hydroperoxydeamination; N-electrophilic amination; solid phase; PEGA resin; 6-hydroxynorleucine; HR MAS NMR;

D O I：

10.1016/S0040-4039(99)01414-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unnatural amino acid Lys(NH2), easily incorporated into a peptidyl-PEGA resin by N-electrophilic amination of the epsilon-amino group, was cleanly transformed on the solid phase into 6-hydroxynorleucine by air oxidation in the presence of bicarbonate ions followed by reduction of the hydroperoxy intermediate with a water soluble phosphine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7315 / 7318

页数：4

共 15 条

[1] DEAMINATION OF PRIMARY AMINES WITH DINITROGEN TETRAOXIDE AT LOW-TEMPERATURES - FORMATION OF NITRATES
BARTON, DHR
NARANG, SC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (09): : 1114 - 1116
[2] BELYAEV AA, 1995, TETRAHEDRON LETT, V28, P439
[3] BONNET D, 1998, IN PRESS J PEPT RES
[4] HANCOCK WS, 1976, ANAL BIOCHEM, V71, P260, DOI 10.1016/0003-2697(76)90034-8
[5] 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
[6] A 2-STAGE CONVERSION OF PRIMARY-ALKYL PRIMARY-AMINES INTO ALCOHOLS AND FURTHER EXAMPLES OF TRANSFUNCTIONALIZATION OF AMINES UNDER MILD CONDITIONS
KATRITZKY, AR
SABA, A
PATEL, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (05): : 1492 - 1494
[7] Klinguer C, 1996, TETRAHEDRON LETT, V37, P7259
[8] PEGA - A FLOW STABLE POLYETHYLENE-GLYCOL DIMETHYL ACRYLAMIDE COPOLYMER FOR SOLID-PHASE SYNTHESIS
MELDAL, M
[J]. TETRAHEDRON LETTERS, 1992, 33 (21) : 3077 - 3080
[9] Chemistry of hydrazinopeptides: a new hydroperoxydeamination process
Melnyk, O
Rommens, C
Gras-Masse, H
[J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1491 - 1494
[10] Melnyk O, 1998, J PEPT RES, V52, P180

← 1 2 →