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Surface-tethered iterative carbohydrate synthesis: a spacer study.


ABSTRACT: Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.

SUBMITTER: Ganesh NV 

PROVIDER: S-EPMC3757931 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Surface-tethered iterative carbohydrate synthesis: a spacer study.

Ganesh N Vijaya NV   Fujikawa Kohki K   Tan Yih Horng YH   Nigudkar Swati S SS   Stine Keith J KJ   Demchenko Alexei V AV  

The Journal of organic chemistry 20130708 14


Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl a  ...[more]

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