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Metabolic products of microorganisms. Part 262 . The absolute configuration of sphydrofuran, a widespread metabolite from streptomycetes
Author(s) -
Bindseil Kai U.,
Henkel Thomas,
Zeeck Axel,
Bur Daniel,
Niederer Daniel,
Séquin Urs
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740617
Subject(s) - chemistry , absolute configuration , tautomer , metabolite , derivative (finance) , stereochemistry , streptomyces , furan , anomer , strain (injury) , molecule , organic chemistry , bacteria , biochemistry , medicine , biology , financial economics , economics , genetics
Sphydrofuran ( 1 ) was isolated from the culture filtrate of Streptomyces sp. (strain Gö 28 and Tü 3616) by chemical screening methods. Metabolite 1 is an anomeric and ring‐chain tautomeric mixture and could easily be transformed into the stable furan derivative 2 under acidic conditions. The constitution and relative configuration of 1 was established by X‐ray crystallography of its 8‐ O ‐methyl derivative 3a. The absolute configuration at C(4) of 1 and thus of the whole molecule (3 R ,4 S ,5 S ) could be determined starting from 2 using the Helmchen method.