Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer

Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer
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DOI:
10.1038/nprot.2007.268
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发表时间:
2007-01-01
期刊:
影响因子:
14.8
通讯作者:
Tirrell, David A.
Tirrell, David A.
中科院分区:
生物学1区
文献类型:
--
作者:
Link, A. James;Vink, Mandy K. S.;Tirrell, David A.

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叠氮官能团近年来在化学生物学研究中发挥了重要作用。叠氮化物可以很容易地被引入蛋白质后,取代蛋氨酸残基与非规范氨基酸叠氮基高丙氨酸(AHA)。该方案描述了一种基于铜催化胺转化为叠氮化物的AHA合成路线。一个替代方案的准备AHA是在一个配套文件。通过本文所述的途径合成和纯化AHA可以在3-4天内完成。
The azide functional group has assumed a prominent role in chemical biology efforts in recent years. Azides may be readily introduced into proteins upon replacement of methionine residues with the non-canonical amino acid azidohomoalanine (AHA). This protocol describes a synthetic route to AHA based on the copper-catalyzed conversion of amines to azides. An alternate protocol for the preparation of AHA is presented in a companion paper. The synthesis and purification of AHA via the route described herein can be completed in 3-4 days.