Synthesis of (S)- and (R)-5-Oxo-piperazine-2-Carboxylic Acid and Its Application to Peptidomimetics

被引：10

作者：

Guitot, Karine ^{[1
,2
]}

Carboni, Stefano ^{[2
]}

Reiser, Oliver ^{[1
]}

Piarulli, Umberto ^{[2
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; PIPECOLIC ACID; ASYMMETRIC-SYNTHESIS; PEPTIDE-BONDS; DERIVATIVES; ENANTIOMERS; RESOLUTION; ANALOGS; MODEL;

D O I：

10.1021/jo901389q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of (S)- and (R)-N-Boc-5-oxopiperazine-2-carboxylic acid is reported starting from L- or D-serine and ethyl glyoxylate. Those were evaluated as constituents in two tetrapeptides by studying their secondary Structure by H-1 NMR spectroscopy. In the case of Boc-Val-(S)-PCA-Gly-Leu-OMe, two readily interconverting conformations (in a 40%: 60% ratio) were observed, differing for the cis-trans isomerizaton of the tertiary amide bond, while Boc-Val-(R)-PCA-Gly-Lcu-OMe displayed an equilibrium between a gamma-turn and it type II beta-turn conformation.

引用

页码：8433 / 8436

页数：4

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