Beumer R, Bubert C, Cabrele C, Vielhauer O, Pietzsch M, Reiser O
Department of Organic Chemistry, University of Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.
J Org Chem. 2000 Dec 29;65(26):8960-9. doi: 10.1021/jo005541l.
The synthesis of diastereo- and enantiomerically pure beta-aminocyclopropanecarboxylic acids (beta-ACCs) is described. Starting from pyrrole, (rac)-4 is readily obtained, which was kinetically resolved by enzymatic hydrolysis. Subsequent oxidation of (-)-4 and deformylation gives rise to the cis-beta-ACC derivative (ent)-9, while (+)-10 was converted to the trans-beta-ACC derivative 8. Both 8 and (ent)-9 and their benzyl esters 13 and 16, being conformationally restricted beta-alanine or gamma-aminobutyric acid (GABA) derivatives, represent useful building blocks for peptides containing unnatural amino acids.
本文描述了非对映体纯和对映体纯的β-氨基环丙烷羧酸（β-ACC）的合成。从吡咯出发，很容易得到（外消旋）-4，通过酶促水解对其进行动力学拆分。随后对（-）-4进行氧化和脱甲酰基反应得到顺式-β-ACC衍生物（对映体）-9，而（+）-10则转化为反式-β-ACC衍生物8。8和（对映体）-9及其苄酯13和16作为构象受限的β-丙氨酸或γ-氨基丁酸（GABA）衍生物，是含有非天然氨基酸的肽的有用构建单元。
