A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy

Jeroen D C Codée; Bas Stubba; Marialuisa Schiattarella; Herman S Overkleeft; Constant A A van Boeckel; Jacques H van Boom; Gijsbert A van der Marel

doi:10.1021/ja045613g

A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy

J Am Chem Soc. 2005 Mar 23;127(11):3767-73. doi: 10.1021/ja045613g.

Authors

Jeroen D C Codée¹, Bas Stubba, Marialuisa Schiattarella, Herman S Overkleeft, Constant A A van Boeckel, Jacques H van Boom, Gijsbert A van der Marel

Affiliation

¹ Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 15771511
DOI: 10.1021/ja045613g

Abstract

A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.

Publication types

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

MeSH terms

Carbohydrate Sequence
Glycosylation
Heparin / chemical synthesis*
Molecular Sequence Data
Oligosaccharides / chemical synthesis*
Uronic Acids / chemical synthesis
Uronic Acids / chemistry

Substances

Oligosaccharides
Uronic Acids
Heparin