Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor

Steven C Zammit; Vito Ferro; Edward Hammond; Mark A Rizzacasa

doi:10.1039/b708594j

Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor

Org Biomol Chem. 2007 Sep 7;5(17):2826-34. doi: 10.1039/b708594j. Epub 2007 Jul 26.

Authors

Steven C Zammit¹, Vito Ferro, Edward Hammond, Mark A Rizzacasa

Affiliation

¹ School of Chemistry, Bio21 Institute, 30 Flemington Rd, The University of Melbourne, Victoria 3010, Australia.

PMID: 17700851
DOI: 10.1039/b708594j

Abstract

The total synthesis of natural (+)-trachyspic acid and its enantiomer is described starting from a common 2-deoxy-d-ribose derivative. The synthesis of the corresponding C3 epimers from the same starting material is also described. Each stereoisomer was assayed for heparanase inhibition.

Publication types

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

MeSH terms

Crystallography, X-Ray
Cyclization
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Glucuronidase / antagonists & inhibitors*
Glucuronidase / metabolism
Models, Molecular
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Spiro Compounds / pharmacology*
Stereoisomerism

Substances

Enzyme Inhibitors
Spiro Compounds
trachyspic acid
heparanase
Glucuronidase