pentasaccharide

A pentasaccharide is a carbohydrate oligosaccharide comprising five monosaccharide units linked by glycosidic bonds. Like other oligosaccharides, pentasaccharides can be linear or branched and may include different sugar types such as glucose, galactose, mannose, N-acetylglucosamine, or fucose. The arrangement of linkages, including whether bonds are alpha or beta and which carbon atoms participate (for example 1→4 or 1→6), determines the molecule’s shape and its potential biological interactions.

In nature, pentasaccharides occur as parts of larger polysaccharides or glycoproteins, or as defined fragments produced during digestion or modification. A well-known bioactive example is a defined pentasaccharide sequence within heparin and related glycosaminoglycans that binds antithrombin III, enhancing inhibition of coagulation factors and contributing to anticoagulant activity. Because of this specificity, well-defined pentasaccharides are also prepared synthetically for research, diagnostics, and potential therapeutic applications.

Synthesis and analysis: Pentasaccharides can be obtained through enzymatic cleavage of longer carbohydrates or by chemical and chemoenzymatic methods that yield homogeneous products with defined sequences and linkages. They are used in glycobiology as standards, in glycan arrays, and to study protein–carbohydrate interactions. In general, pentasaccharides represent an intermediate length category within oligosaccharides (shorter than hexasaccharides, longer than disaccharides), with properties that depend on their precise monosaccharide composition and linkage pattern.