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Stereoselective synthesis of stable isotope‐labeled L‐α‐amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L‐[ 15 N]alanine, L‐[ 15 N]valine, L‐[ 15 N]leucine, L‐[ 15 N]phenylalanine and L‐[1‐ 13 C, 15 N]valine
Author(s) -
Lodwig Siegfried N.,
Unkefer Clifford J.
Publication year - 1996
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/(sici)1099-1344(199603)38:3<239::aid-jlcr831>3.0.co;2-e
Subject(s) - chemistry , stereoselectivity , amino acid , phenylalanine , valine , isotopomers , stereochemistry , leucine , alanine , organic chemistry , biochemistry , catalysis , molecule
Using 1‐chloro‐1‐[ 15 N]nitrosocyclohexane, we have prepared five L‐[α‐ 15 N]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 13 C and/or 15 N isotopomers of α‐amino acids.