Asymmetric synthesis and translational competence of L-alpha-(1-cyclobutenyl)glycine.
Asymmetric synthesis and translational competence of L-alpha-(1-cyclobutenyl)glycine.
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DOI：
10.1021/ol049026b
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发表时间：
2004-09
期刊：
影响因子：
5.2
通讯作者：
L. Jayathilaka;Mahua Deb;R. Standaert
中科院分区：
文献类型：
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作者：
L. Jayathilaka;Mahua Deb;R. Standaert
[反应：L-α-（1-环丁烯基）甘氨酸（1-Cbg）是异亮氨酸和缬氨酸的潜在可翻译类似物，也是肽的有用结构单元。以（S）-叔丁烷亚磺酰亚胺和乙醛酸叔丁酯为原料，通过1-环丁烯基溴化镁与亚磺酰亚胺2b的非对映选择性加成反应，实现了对映选择性合成。1-在体外转译绿色荧光蛋白时，Cbg可以有效地取代异亮氨酸和缬氨酸，但不能取代亮氨酸。
[reaction: see text] 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.