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Xialenons, New Pentalenons from Streptomyces
Author(s) -
Tang YuanQing,
Sattler Isabel,
Thiericke Ralf,
Grabley Susanne,
Feng XiaoZhang
Publication year - 2000
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 - 10.1002/1099-0690(200007)2000:13<2401::aid-ejoc2401>3.0.co;2-y
Subject(s) - chemistry , derivatization , ketone , double bond , stereochemistry , side chain , streptomyces , chemical synthesis , absolute configuration , chemical structure , strain (injury) , organic chemistry , high performance liquid chromatography , biochemistry , medicine , biology , bacteria , in vitro , genetics , polymer
New pentalenons, named xialenon A to E ( 1 to 5 ), were discovered by a chemical screening of the culture broth of the Streptomyces sp. (strain GT 061169). The chemical structures of these secondary metabolites were determined by detailed spectroscopic investigation as well as chemical derivatization reactions. The absolute stereochemistry of 1 was determined by esterification with chiral acids via Helmchen’s method. A common structural element of the xialenons is an α,β‐unsaturated ketone in one of the two fused 5‐membered rings (reduced double bond in 1 ), that is substituted with both, a hydroxyl group in α‐position, and an additional allyl side chain in β‐position.