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6‐Deoxy‐α‐ L ‐talopyranosides from Streptomyces sp.
Author(s) -
Bitzer Jens,
Zeeck Axel
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600221
Subject(s) - chemistry , glycoside , phenols , stereochemistry , biosynthesis , streptomyces , aryl , organic chemistry , bacteria , enzyme , alkyl , biology , genetics
Streptomyces sp. strain GöM1 was found to produce seven novel glycosides ( 2 – 8 ) containing the rare deoxysugar 6‐deoxy‐α‐ L ‐talose. The aglycones are small phenols, isovaleric acid or aromatic carboxylic acids. By precursor‐directed biosynthesis, the yields of the compounds could be increased significantly. Feeding of 4‐hydroxybenzoic acid led to the production of both acyl and aryl glycosides, and of compound 9 with both structural elements. Pyrrol‐2‐ylcarbonyl 6‐deoxy‐α‐ L ‐talopyranoside ( 6 ) shows remarkable growth inhibition of some parasites. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)