Stereochemical Control in Carbohydrate Chemistry

Emma M. Dangerfield and Bridget L. Stocker
The Malaghan Institute Medical Research, Wellington, New Zealand
Rhys Batchelor , Peter T. Northcote and Joanne E. Harvey
School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington, New Zealand
J. Chem. Educ., 2008, 85 (5), p 689
DOI: 10.1021/ed085p689
Publication Date (Web): May 1, 2008

Abstract

Carbohydrates, in the form of glycoconjugates, have recently been shown to control a wide range of cellular processes. Accordingly, students interested in the study of organic chemistry and biomedical sciences should be exposed to carbohydrate chemistry. To this end, we have developed a sequence of experiments that leads the student from the derivatization of naturally occurring D-glucose through to the formation of simple alkyl and aryl glycosides, and in doing so this experiment provides a comprehensive overview of the fundamentals of glycoside synthesis. These experiments focus on the control of stereochemistry at the anomeric center and NMR spectroscopy for the structural elucidation of products.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carbohydrates
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History

  • Received: August 03, 2009

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