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Biosynthesis of tritium, deuterium and carbon‐13 labeled cycloheximide
Author(s) -
Hsi Richard S. P.,
Witz Dennis F.,
Stolle Wayne T.,
Baczynskyj Lubomir,
Scahill Terrence A.
Publication year - 1980
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.2580170503
Subject(s) - cycloheximide , chemistry , deuterium , tritium , streptomyces griseus , carbon 14 , radiochemistry , isotope , carbon fibers , methionine , amino acid , protein biosynthesis , biochemistry , streptomyces , bacteria , physics , materials science , quantum mechanics , biology , composite number , nuclear physics , composite material , genetics
Tritium, deuterium, and carbon‐13 labeled cycloheximide were prepared through fermentation of Streptomyces griseus in the presence of S‐methyl labeled L‐methionine. Cycloheximide‐ 3 H of specific activity 4.96 mCi/mg (1.40 Ci/mmol) was obtained in 25% overall radiochemical yield. Nuclear magnetic resonance and mass spectral analyses of the deuterium and carbon‐13 labeled products showed that isotope incorporation occurred virtually exclusively in the two methyl groups in cycloheximide, with negligible (<5%) incorporation in the rest of the molecule. Furthermore, deuterated species contained either three or six deuterium atoms, indicating that the methyl groups were transferred intact from L‐methionine. Also, the two methyl groups in cycloheximide were of equal isotope enrichment. The overall enrichment achieved in the methyl groups was 55% and 45%, respectively, in the deuterium and carbon‐13 labeled compounds.