Table of Contents
International Journal of Carbohydrate Chemistry
Volume 2016 (2016), Article ID 4760548, 42 pages
http://dx.doi.org/10.1155/2016/4760548
Review Article

Biosynthesis and Biological Activity of Carbasugars

Facultad de Química, Departamento de Química Orgánica, Universidad Complutense, Ciudad Universitaria, 28040 Madrid, Spain

Received 13 March 2016; Accepted 15 May 2016

Academic Editor: Sławomir Jarosz

Copyright © 2016 Silvia Roscales and Joaquín Plumet. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland’s group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.