Publication

Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases

Pierre Vogel
2002
Journal Articles

Abstract

An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3.5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to Our expectations, (1 S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the beta-D-mannopyranose configuration for C(1)-C(5) inhibits alpha- and beta-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the alpha-D-glucopyranose configuration, is not recognised by these enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/ea30caaa-b54a-4590-a380-af7afd60107d

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Pierre Vogel
2002
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/ea30caaa-b54a-4590-a380-af7afd60107d

About this result

Related concepts (17)

Anomer

In carbohydrate chemistry, a pair of anomers () is a pair of near-identical stereoisomers or diastereomers that differ at only the anomeric carbon, the carbon that bears the aldehyde or ketone functional group in the sugar's open-chain form. However, in order for anomers to exist, the sugar must be in its cyclic form, since in open-chain form, the anomeric carbon is planar and thus achiral. More formally stated, then, an anomer is an epimer at the hemiacetal/hemiketal carbon in a cyclic saccharide.

Glucose

Glucose is a sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen.

Monosaccharide

Monosaccharides (from Greek monos: single, sacchar: sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-soluble, and crystalline solids. Contrary to their name (sugars), only some monosaccharides have a sweet taste. Most monosaccharides have the formula (CH2O) (though not all molecules with this formula are monosaccharides). Examples of monosaccharides include glucose (dextrose), fructose (levulose), and galactose.