Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

Giuseppe Macchione; José L de Paz; Pedro M Nieto

doi:10.1016/j.carres.2014.05.007

Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

Carbohydr Res. 2014 Jul 23:394:17-25. doi: 10.1016/j.carres.2014.05.007. Epub 2014 May 20.

Authors

Giuseppe Macchione¹, José L de Paz², Pedro M Nieto¹

Affiliations

¹ Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain.
² Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain. Electronic address: [email protected].

PMID: 24930061
DOI: 10.1016/j.carres.2014.05.007

Abstract

The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared.

Keywords: Carbohydrates; Fluorous tag; Glucuronic acid; Glycosylation; Hyaluronic acid; Oligosaccharide synthesis.

Publication types

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

MeSH terms

Carbohydrate Sequence
Chemistry Techniques, Synthetic
Glycosylation
Hyaluronic Acid / chemistry*
Molecular Sequence Data
Oligosaccharides / chemical synthesis*
Trisaccharides / chemical synthesis

Substances

Oligosaccharides
Trisaccharides
Hyaluronic Acid