Colitose

Biological role

Colitose is found in the O-antigen of certain Gram-negative bacteria such as Escherichia coli, Yersinia pseudotuberculosis, Salmonella enterica, Vibrio cholerae, and in marine bacteria such as Pseudoalteromonas sp. The sugar was first isolated in 1958, and subsequently was enzymatically synthesized in 1962.

Biosynthesis

The resulting product, GDP-L-colitose, is then incorporated into the O-antigen by glycosyltransferases and O-antigen processing proteins. Further reactions join the O-antigen to the core polysaccharide to form the full lipopolysaccharide.

GDP-4-keto-6-deoxymannose-3-dehydratase (ColD)

ColD is a PLP-dependent enzyme responsible for the removal of the C-3' hydroxyl group during the biosynthesis of GDP-colitose. It is a product of the Wbdk or ColD genes in Escherichia coli O55 or Salmonella enterica, respectively, and is commonly referred to as ColD.

Usage in biotechnology

Although the sugar is relatively rare, recent work with glycosyltransferases suggests that obscure sugars such as colitose can be incorporated into existing natural-product scaffolds, thereby constructing novel and potentially therapeutic compounds.

References

References

1. (November 2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydrate Research.
2. (June 2001). "Structure of a colitose-containing O-specific polysaccharide of the marine bacterium Pseudoalteromonas tetraodonis IAM 14160(T)". Carbohydrate Research.
3. (1958). "[Colitose, 3-desoxy-L-fucose, a new sugar building block with immunospecific functions in the endotoxins, lipopolysaccharides, of some gram-negative bacteria.]". Biochemische Zeitschrift.
4. (July 1962). "The enzymatic synthesis of guanosine diphosphate colitose by a mutant strain of Escherichia coli". Proceedings of the National Academy of Sciences of the United States of America.
5. (December 2004). "Biosynthesis of colitose: expression, purification, and mechanistic characterization of GDP-4-keto-6-deoxy-D-mannose-3-dehydrase (ColD) and GDP-L-colitose synthase (ColC)". Biochemistry.
6. (September 2006). "Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions". Science.