STEREOSELECTIVE SYNTHESIS OF STABLE ISOTOPE-LABELED L-ALPHA-AMINO ACIDS - CHEMOMICROBIOLOGICAL SYNTHESIS OF L-[BETA-C-13]-TRYPTOPHAN, L-[2'-C-13]-TRYPTOPHAN, AND L-[1'-N-15]TRYPTOPHAN

被引:11
|
作者
UNKEFER, CJ [1 ]
LODWIG, SN [1 ]
SILKS, LA [1 ]
HANNERS, JL [1 ]
EHLER, DS [1 ]
GIBSON, R [1 ]
机构
[1] CENTRALIA COLL, DIV SCI, CENTRALIA, WA 98531 USA
关键词
L-[BETA-C-13]TRYPTOPHAN; L-[2'-C-13]TRYPTOPHAN; L-[1'-N-15]TRYPTOPHAN; L-[BETA-C-13]SERINE; 1-N-15]INDOLE; AND; 2-C-13]INDOLE;
D O I
10.1002/jlcr.2580291109
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
We have developed a stereospecific chemomicrobiological synthesis of labeled tryptophan. L-[3-C-13]Serine, [1-N-15]- and [2-C-13]indole were used as precursors for the synthesis of L-[beta-C-13]-, L-[1'-N-15]-, and L-[2'-C-13]tryptophan, respectively. The labeled precursors were incorporated quantitatively into tryptophan using a strain of E. coli engineered to overproduce tryptophan synthase. Labeled indoles were prepared by the base-promoted cyclization of appropriately labeled N-formyl-o-toluide; serine was prepared biosynthetically as described previously.
引用
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页码:1247 / 1256
页数:10
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