Asymmetric synthesis and translational competence of L-α-(1-cyclobutenyl)glycine

被引：20

作者：

Jayathilaka, LP ^{[1
]}

Deb, M ^{[1
]}

Standaert, RF ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol049026b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-alpha-(1-Cyclobutenyl)glycine (1-Cbg) was targeted as a potentially translatable analogue of isoleucine and valine and as a useful building block for peptides. An enantioselective synthesis was executed in which the key step was diastereoselective addition of 1-cyclobutenylmagnesium bromide to the sulfinimine 2b derived from (S)-t-butanesulfinimide and tert-butyl glyoxylate. 1-Cbg was found to substitute efficiently for isoleucine and valine, but not leucine, in the translation of green fluorescent protein in vitro.

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页码：3659 / 3662

页数：4

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