ChemInform Abstract: Recent Advances in the Synthesis of Carbohydrate Mimetics

Koester, Dennis C.; Holkenbrink, Annika; Werz, Daniel B.

doi:10.1002/chin.201102244

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“…On this basis, the search for new carbohydrate derivatives with analogous or even improved biological properties compared to those of the parent structures (carbohydrate mimetics) [40][41][42][43] appears to be an attractive matter of research. The carbasugars (initially, the term pseudosugars was coined for this family of compounds, although they are currently known as carbasugars [44]), compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene group (Figure 1), fall within this category [45][46][47][48][49].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis and Biological Activity of Carbasugars

Roscales

Plumet

2016

International Journal of Carbohydrate Chemistry

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The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland's group.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.

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