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Stereoselective synthesis of stable isotope‐labeled L‐α‐amino acids: Chemomicrobiological synthesis of L‐[β‐ 13 C]‐, L‐[2′‐ 13 C]‐, and L‐[1′ 15 N]tryptophan
Author(s) -
Unkefer Clifford J.,
Lodwig Siegfried N.,
Silks Louis A.,
Hanners John L.,
Ehler Deborah S.,
Gibson Rowena
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580291109
Subject(s) - chemistry , tryptophan , tryptophan synthase , stereospecificity , stereochemistry , indole test , serine , stereoselectivity , amino acid , biochemistry , catalysis , enzyme
Abstract We have developed a stereospecific chemomicrobiological synthesis of labeled tryptophan. L‐[3‐ 13 C]Serine, [1‐ 15 N]‐ and [2‐ 13 C]indole were used as precursors for the synthesis of L‐[β‐ 13 C]‐, L‐[1′‐ 15 N]‐, and L‐[2′‐ 13 C]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.