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Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker.


ABSTRACT: A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone.

SUBMITTER: Zhang J 

PROVIDER: S-EPMC3775522 | biostudies-other | 2013 Aug

REPOSITORIES: biostudies-other

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Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker.

Zhang Junfeng J   Zou Lu L   Lowary Todd L TL  

ChemistryOpen 20130711 4


A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone. ...[more]

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