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一种用于掺入肽光亲和试剂的产卡宾氨基酸。

A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.

作者信息

Shih L B, Bayley H

出版信息

Anal Biochem. 1985 Jan;144(1):132-41. doi: 10.1016/0003-2697(85)90094-6.

DOI:10.1016/0003-2697(85)90094-6
PMID:3985309
Abstract

3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol. The alcohol was converted to 3-(alpha-iodo-p-tolyl)-3-(trifluoromethyl)-3H-diazirine, which was used to alkylate N-(diphenylmethylene)glycine ethyl ester. After deprotection the amino acid was obtained with an overall yield of 18%. The D- and L-isomers of 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine have also been resolved, and 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine labeled with tritium has been prepared. The advantages of using this amino acid as a building block for peptide photoaffinity reagents is discussed.

摘要

3-[对-[3-(三氟甲基)-3H-重氮丙啶-3-基]苯基]丙氨酸已由对溴苄醇经10步反应制备而成。该醇被转化为3-(α-碘对甲苯基)-3-(三氟甲基)-3H-重氮丙啶，用于使N-(二苯基亚甲基)甘氨酸乙酯烷基化。脱保护后得到该氨基酸，总产率为18%。3-[对-[3-(三氟甲基)-3H-重氮丙啶-3-基]苯基]丙氨酸的D-和L-异构体也已拆分出来，并且制备了用氚标记的3-[对-[3-(三氟甲基)-3H-重氮丙啶-3-基]苯基]丙氨酸。讨论了使用这种氨基酸作为肽光亲和试剂构建单元的优点。

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