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RESEARCH ARTICLE
Contents Vol 67(3)

Boric Acid Catalyzed Methyl Esterification of Sugar Acids

Stephan M. Levonis A , Brighid B. Pappin A , Alissa Sharp A , Milton J. Kiefel A B and Todd A. Houston A B
+ Author Affiliations
- Author Affiliations

A Institute for Glycomics and School of Biomolecular and Physical Sciences, Gold Coast Campus, Griffith University, Qld 4222, Australia.

B Corresponding authors. Email: M.Kiefel@griffith.edu.au; T.Houston@griffith.edu.au

Australian Journal of Chemistry 67(3) 528-530 https://doi.org/10.1071/CH13459
Submitted: 31 August 2013  Accepted: 3 December 2013   Published: 18 December 2013

Abstract

Boric acid catalyzes methyl esterification of certain sugar acids (sialic acid, deaminated neuraminic acid) and related natural products (quinic acid) quite cleanly in some cases. However, closely related sugar acids (glucuronic acid, 3-deoxy-d-manno-oct-2-ulosonic acid) failed to esterify under the same conditions. Factors governing this dichotomy are discussed.


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