Unprecedented 1,1′-carbonyldiimidazole-mediated amidation of unprotected α-amino acids in water

被引：15

作者：

Sharma, Rohit K. ^{[1
]}

Jain, Rahul ^{[1
]}

机构：

[1] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Nagar 160062, Punjab, India

来源：

SYNLETT | 2007年 / 04期

关键词：

amidation; 1,1 '-carbonyldiimidazole (CDI); alpha-amino acids; amidation reaction in water;

D O I：

10.1055/s-2007-967965

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first amidation reaction of unprotected a-amino acids in water under neutral conditions with various aliphatic, aromatic and heteroaromatic amines in the presence of coupling reagent 1,1'-carbonyldiimidazole at ambient temperature is described.

引用

页码：603 / 606

页数：4

共 33 条

[1] Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids [J].

Bode, JW ;

Fox, RM ;

Baucom, KD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1248-1252

[2] Iterative, aqueous synthesis of β3-oligopeptides without coupling reagents [J].

Carrillo, N ;

Davalos, EA ;

Russak, JA ;

Bode, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1452-1453

[3] Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands [J].

Chu, WH ;

Tu, Z ;

McElveen, E ;

Xu, JB ;

Taylor, M ;

Luedtke, RR ;

Mach, RH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :77-87

[4] The process development of a scaleable route to the PDE5 inhibitor UK-357,903 [J].

Dale, DJ ;

Draper, J ;

Dunn, PJ ;

Hughes, ML ;

Hussain, F ;

Levett, PC ;

Ward, GB ;

Wood, AS .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (06) :767-772

[5] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

[6] Modulation of reactivity in native chemical ligation through the use of thiol additives [J].

Dawson, PE ;

Churchill, MJ ;

Ghadiri, MR ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4325-4329

[7] Synthesis of native proteins by chemical ligation [J].

Dawson, PE ;

Kent, SBH .

ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960

[8]

Fiona L. L., 2005, J AM CHEM SOC, V127, P2686

[9] URETHANE-PROTECTED AMINO-ACID N-CARBOXY ANHYDRIDES AND THEIR USE IN PEPTIDE-SYNTHESIS [J].

FULLER, WD ;

COHEN, MP ;

SHABANKAREH, M ;

BLAIR, RK ;

GOODMAN, M ;

NAIDER, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7414-7416

[10] Synthesis of a novel esterase-sensitive cyclic prodrug of a hexapeptide using an (acyloxy)alkoxy promoiety [J].

Gangwar, S ;

Pauletti, GM ;

Siahaan, TJ ;

Stella, VJ ;

Borchardt, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1356-1362

← 1 2 3 4 →