Synthesis of unsaturated analogues of glutamic acid: Amination of trianions from unsaturated dicarboxylic acids with chloramine

被引：10

作者：

Allan, RD ^{[1
]}

Duke, RK ^{[1
]}

Hambley, TW ^{[1
]}

Johnston, GAR ^{[1
]}

Mewett, KN ^{[1
]}

Quickert, N ^{[1
]}

Tran, HW ^{[1
]}

机构：

[1] UNIV SYDNEY,SCH CHEM,SYDNEY,NSW 2006,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1996年 / 49卷 / 07期

关键词：

D O I：

10.1071/CH9960785

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trianions can be formed from dicarboxylic acids which contain a beta,gamma-double bond, and amination with chloramine yields beta,gamma-unsaturated alpha-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (+/-)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P2(1)/c, a 9.245(24), b 8.455(2), c 9.311(3) Angstrom, beta 95.00(2)degrees, and the structure was refined to R 0.035 for 980 F.

引用

页码：785 / 791

页数：7

共 28 条

[1] STRUCTURE-ACTIVITY STUDIES ON THE ACTIVITY OF A SERIES OF CYCLOPENTANE GABA ANALOGS ON GABA-A RECEPTORS AND GABA UPTAKE [J].