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Biosynthesis of Gabosines A, B, and C, Carba Sugars from Streptomyces cellulosae
Author(s) -
Höfs Regina,
Schoppe Silke,
Thiericke Ralf,
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(200005)2000:10<1883::aid-ejoc1883>3.0.co;2-q
Subject(s) - shikimic acid , chemistry , biosynthesis , shikimate pathway , stereochemistry , biochemistry , sugar phosphates , aminocyclitol , pentose phosphate pathway , moiety , pentose , actinomycetales , phosphate , streptomycetaceae , carbohydrate synthesis , metabolic pathway , streptomyces , metabolism , carbohydrate , fermentation , enzyme , bacteria , glycolysis , biology , antibiotics , aminoglycoside , genetics
The biosynthesis of the gabosines A−C ( 3−5 ) was studied by feeding cultures of Streptomyces cellulosae subsp. griseorubiginosus (strain S 1096) with 13 C‐labeled precursors. Although the carba sugars are structurally related to shikimic acid, the biosynthetic origin was found to be different to the shikimate pathway. The results revealed that the gabosines are formed via a pentose phosphate pathway by cyclization of a heptulose phosphate intermediate. This intermediate arises from a triose phosphate by successive transfer of two C 2 fragments by transketolases. This pathway is identical as that described for valienamine ( 7 ), the aminocarba sugar moiety of validamycin, and acarbose ( 2 ). The results from biosynthetic studies are discussed on the background of the variety of gabosines found in nature.