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Chemical synthesis of labelled intermediates in cyanogenic glucoside biosynthesis
Author(s) -
Møller Birger Lindberg
Publication year - 1978
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.2580140504
Subject(s) - chemistry , sodium cyanoborohydride , oxime , hydroxylamine , tyrosine , biosynthesis , trimethylsilyl , ammonia , dehydration , organic chemistry , glucoside , stereochemistry , biochemistry , enzyme , medicine , alternative medicine , pathology
Abstract Chemical syntheses of [UL‐ 14 C]‐labelled N‐hydroxytyrosine, p‐hydroxyphenylpyruvic acid oxime, p‐hydroxyphenylacetaldoxime, and p‐hydroxyphenylacetonitrile in high yields from L‐[UL‐ 14 C]‐tyrosine are described. These syntheses involve initial conversion of L‐tyrosine to p‐hydroxyphenylpyruvic acid, which then is allowed to react with hydroxylamine to form p‐hydroxypheny lpyruvic acid oxime. N‐Hydroxytyrosine is obtained from the latter by reduction with sodium cyanoborohydride, and is oxidatively decar‐boxylated to p‐hydroxyphenylacetaldoxime by treatment with ammonia. Finally, p‐hydroxyphenylacetonitrile is obtained by dehydration of the aldoxime with thionylchloride. All synthesized compounds were identified by combined GLC/MS of their trimethylsilyl derivatives. The commercial availability of several specifically labelled 14 C, 2 H, and 3 H tyrosines and of 2 H and 3 H sodium cyanoborohydride makes the method equally useful for synthesis of various specifically labelled compounds.