Gram-scale syntheses of the (1-->3)-linked and (1-->4)-linked hyaluronan disaccharides

Sara L Adamski-Werner; Bryan K S Yeung; Lynne A Miller-Deist; Peter A Petillo

doi:10.1016/j.carres.2004.03.005

Gram-scale syntheses of the (1-->3)-linked and (1-->4)-linked hyaluronan disaccharides

Carbohydr Res. 2004 May 17;339(7):1255-62. doi: 10.1016/j.carres.2004.03.005.

Authors

Sara L Adamski-Werner¹, Bryan K S Yeung, Lynne A Miller-Deist, Peter A Petillo

Affiliation

¹ Department of Chemistry, University of Illinois, 600 S. Mathews Ave., Urbana, IL 61801, USA.

PMID: 15113662
DOI: 10.1016/j.carres.2004.03.005

Abstract

The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1-->4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1-->3)-linked disaccharide 18 was achieved in 7% overall yield utilizing acetonide protection in addition to the chlorosilane-induced carbamate cleavage methodology and the TEMPO oxidation.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Disaccharides / chemical synthesis*
Disaccharides / chemistry
Hyaluronic Acid / chemistry*
Molecular Structure

Substances

Disaccharides
Hyaluronic Acid