An Empirical Understanding of the Glycosylation Reaction

Sourav Chatterjee, Sooyeon Moon, Felix Hentschel, Kerry Gilmore, Peter H. Seeberger

Research output: Contribution to journalArticlepeer-review

91 Citations (SciVal)

Abstract

Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.

Original languageEnglish
Pages (from-to)11942-11953
Number of pages12
JournalJournal of the American Chemical Society
Volume140
Issue number38
DOIs
Publication statusPublished - 26 Sept 2018

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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