Stereoselective synthesis of stable isotope-labeled L-alpha-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[N-15]alanine, L-[N-15]valine, L-[N-15]leucine, L-[N-15]phenylalanine and L-[1-C-13,N-15]valine.

被引：0

作者：

Lodwig, SN

Unkefer, CJ

机构：

[1] LOS ALAMOS NATL LAB,LOS ALAMOS,NM 87545

[2] CENTRALIA COLL,DIV SCI,CENTRALIA,WA 98531

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 1996年 / 38卷 / 03期

关键词：

1-chloro-1-[N-15]nitrosocyclohexane; L-[N-15]alanine; L-[N-15]valine; L-[N-15]leucine; L-[N-15]phenylalanine; L-[1-C-13; N-15]valine; bornane-10,2-sultam; camphor-l0-2-sultam;

D O I：

10.1002/(SICI)1099-1344(199603)38:3<239::AID-JLCR831>3.0.CO;2-E

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Using 1-chloro-1-[N-15]nitrosocyclohexane, we have prepared five L-[alpha-N-15]amino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-10,2-sultams, followed by Zn-o/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5% e.e. By starting with labeled (S)-acylbornane-10,2-sultams this stereoselective route could be to prepare many C-13 and/or N-15 isotopomers of alpha-amino acids.

引用

页码：239 / 248

页数：10

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