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A Chemoenzymatic Total Synthesis of the Neurogenic Starfish Ganglioside LLG‐3 Using an Engineered and Evolved Synthase
Author(s) -
Rich Jamie R.,
Withers Stephen G.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204578
Subject(s) - starfish , ganglioside , chemistry , stereochemistry , oligosaccharide , total synthesis , atp synthase , biochemistry , enzyme , combinatorial chemistry , biology , ecology
An LLG‐3 oligosaccharide–fluoride (see scheme) can be assembled chemoenzymatically and readily coupled with various sphingosines by an engineered endoglycoceramidase glycosynthase. The lyso ganglioside products are acylated to generate the individual isomers identified in the heterogeneous natural isolates, as well as modified glycosphingolipids.