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Combined chemical and biosynthetic route to access a new apoptolidin congener.


ABSTRACT: Glycosylation of a synthetic aglycone using precursor-directed biosynthesis is facilitated by a chemical ketosynthase "knockdown" of the apoptolidin producer Nocardiopsis sp. This synthetic approach facilitated the preparation of an unnatural disaccharide derivative of apoptolidin D that substantially restores cytotoxicity against H292 cells and deconvolutes the role of the decorating sugars in apoptolidin bioactivity.

SUBMITTER: Ghidu VP 

PROVIDER: S-EPMC2720611 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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Combined chemical and biosynthetic route to access a new apoptolidin congener.

Ghidu Victor P VP   Ntai Ioanna I   Wang Jingqi J   Jacobs Aaron T AT   Marnett Lawrence J LJ   Bachmann Brian O BO   Sulikowski Gary A GA  

Organic letters 20090701 14


Glycosylation of a synthetic aglycone using precursor-directed biosynthesis is facilitated by a chemical ketosynthase "knockdown" of the apoptolidin producer Nocardiopsis sp. This synthetic approach facilitated the preparation of an unnatural disaccharide derivative of apoptolidin D that substantially restores cytotoxicity against H292 cells and deconvolutes the role of the decorating sugars in apoptolidin bioactivity. ...[more]

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