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Synthesis of [7‐ 3 H]valienamine, [7‐ 3 H]valienone, [7‐ 3 H]valiolamine and [7‐ 3 H]valiolone from validamycin A
Author(s) -
Lee Sungsook,
Tornus Ingo,
Dong Haijun,
Gröger Stefan
Publication year - 1999
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(199904)42:4<361::aid-jlcr197>3.0.co;2-#
Subject(s) - chemistry , radiochemistry , stereochemistry
To investigate the biosynthetic pathway to the cyclitol moieties of acarbose and validamycin A, [7‐ 3 H]valienamine, [7‐ 3 H]valienone, [7‐ 3 H]valiolamine and [7‐ 3 H]valiolone were synthesized as plausible precursors. Valienamine together with validamine was isolated from the degradation of validamycin A by Flavobacterium saccharophilum and served as starting material for the synthesis. Validamine was removed partially at the stage of tritylation and completely after the oxidation of the primary hydroxy group at C‐7 to the aldehyde. The resulting valienamine aldehyde was reduced with tritiated sodium borohydride to produce [7‐ 3 H]valienamine. The latter was converted to [7‐ 3 H]valiolamine by a synthetic route described in the literature. The 3 H‐labeled amines were oxidized to [7‐ 3 H]valienone and [7‐ 3 H]valiolone, respectively, using 3,5‐di‐ tert ‐butyl‐1,2‐bezoquinone (DBQ) followed by hydrolysis with oxalic acid. Copyright © 1999 John Wiley & Sons, Ltd.