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MetaCyc Pathway: CDP-ascarylose biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Carbohydrates Biosynthesis Sugars Biosynthesis Sugar Nucleotides Biosynthesis CDP-sugar Biosynthesis
Biosynthesis Cell Structures Biosynthesis Lipopolysaccharide Biosynthesis O-Antigen Biosynthesis

Some taxa known to possess this pathway include ? : Yersinia pseudotuberculosis

Expected Taxonomic Range: Enterobacteriales

Summary:
General Background

A limited number of species of Gram-negative bacteria, all in the family Enterobacteriaceae, utilize unusual sugars, derivatives of 3,6-dideoxyhexose, as an O-antigen of their lipopolysaccharides. These sugars are the dominant antigenic determinants in the membranes of these organisms.

Out of the eight possible stereoisomers of 3,6-dideoxyhexoses, only five have been identified in nature. These are D-abequose, L-ascarylose, β-L-colitose, D-paratose and D-tyvelose. All five 3,6-dideoxyhexoses have been found in different serovars of Yersinia pseudotuberculosis, while other genera possess only some of them. For example, Salmonella enterica enterica serovar Typhimurium group B contains D-abequose, Salmonella enterica enterica serovar Paratyphi A str. ATCC 9150 contains D-paratose and Salmonella enterica enterica serovar Typhi contains D-tyvelose [Thorson94].

These sugars are synthesized via a complex series of enzymatic reactions starting, in most cases, from CDP-α-D-glucose, derived from α-D-glucose 1-phosphate. In a reaction catalyzed by the NAD+-dependent CDP-D-glucose-4,6-dehydratase, CDP-α-D-glucose is converted to CDP-4-dehydro-6-deoxy-D-glucose, which is then converted to the intermediate CDP-4-dehydro-3,6-dideoxy-D-glucose in two consecutive enzymatic reactions, mediated by two components of the CDP-4-dehydro-6-deoxyglucose reductase enzyme complex. The first component is CDP-6-deoxy-L-threo-D-glycero-4-hexulose-3-dehydrase (E1), a pyridoxamine 5'-phosphate (PMP)-linked iron-sulfur-containing catalyst, while the second component is CDP-6-deoxy-L-threo-D-glycero-4-hexulose-3-dehydrase reductase (E3), a [2Fe-2S]-containing flavoprotein.

The product of this complex, CDP-4-dehydro-3,6-dideoxy-D-glucose, is the parent to all five 3,6-dideoxyhexoses.

About This Pathway

CDP-ascarylose, found in Yersinia pseudotuberculosis, is produced by the successive action of two enzymes: CDP-3, 6-dideoxy-D-glycero-D-glycero-4-hexulose-5-epimerase inverts the configuration of its substrate, CDP-4-dehydro-3,6-dideoxy-D-glucose, at carbon C-5, while CDP-3, 6-dideoxy-D-glycero-L-glycero-4-hexulose-4-reductase catalyzes a stereospecific reduction at carbon C-4, yielding CDP-ascarylose [Thorson93].

Superpathways: superpathway of CDP-glucose-derived O-antigen building blocks biosynthesis

Credits:
Created 04-Mar-2008 by Caspi R , SRI International


References

Lerouge02: Lerouge I, Vanderleyden J (2002). "O-antigen structural variation: mechanisms and possible roles in animal/plant-microbe interactions." FEMS Microbiol Rev 26(1);17-47. PMID: 12007641

Thorson93: Thorson, J.S., Lo, S.F., Liu, H.W. (1993). "Molecular basis of 3,6-dideoxyhexose biosynthesis: elucidation of CDP-ascarylose biosynthetic genes and their relationship to other 3,6-dideoxyhexose pathways." J. Am. Chem. Soc. 115:5827-5828.

Thorson94: Thorson JS, Lo SF, Ploux O, He X, Liu HW (1994). "Studies of the biosynthesis of 3,6-dideoxyhexoses: molecular cloning and characterization of the asc (ascarylose) region from Yersinia pseudotuberculosis serogroup VA." J Bacteriol 176(17);5483-93. PMID: 8071227

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Hallis98: Hallis TM, Lei Y, Que NL, Liu H (1998). "Mechanistic studies of the biosynthesis of paratose: purification and characterization of CDP-paratose synthase." Biochemistry 37(14);4935-45. PMID: 9538012

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Nov 22, 2014, BIOCYC14A.