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Structure and Biosynthesis of Mutolide, a Novel Macrolide from a UV Mutant of the Fungus F‐24′707
Author(s) -
Bode Helge Björn,
Walker Martina,
Zeeck Axel
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/(sici)1099-0690(200004)2000:8<1451::aid-ejoc1451>3.0.co;2-f
Subject(s) - chemistry , metabolite , fungus , malonate , strain (injury) , stereochemistry , carbon skeleton , biosynthesis , mutant , mutagenesis , biochemistry , enzyme , botany , biology , gene , anatomy
Abstract The 14‐membered macrolide, mutolide ( 1 ), was discovered by chemical screening of the culture broth of the fungus F‐24′707y, obtained after UV mutagenesis of the wild type strain, which normally produces the spirobisnaphthalene cladospirone bisepoxide ( 2 ). The structure of 1 was established by detailed spectroscopic analysis, X‐ray analysis and derivatisation. The biogenetic origin of the carbon skeleton and the hydroxy groups was verified by feeding sodium [1‐ 13 C]acetate and 18 O 2 to growing cultures of the fungus. Macrolide 1 is generated from acetate/malonate only. The unexpected change of the normal metabolite pattern of this strain is discussed, and proves the value of the OSMAC method.