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Sulikowski Lab

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

AUTHORS

Ghidu VPVictor P , Ntai I Ioanna , Wang J Jingqi , Jacobs AT Aaron T , Marnett LJ Lawrence J , Bachmann BO Brian O , Sulikowski GA Gary A . Organic letters. 2009 7 16; 11(14). 3032-4

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.

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.