Genome Property Definition Page

Accession

GenProp0796

Name

CMP-pseudaminic acid biosynthesis from UDP-N-acetylglucosamine

Type

METAPATH

Description

Pseudaminic acid is a component of the O-antigen of certain pseudomonas strains [1] as well as the glycosylation modification of Campylobacter and Helicobacter flagellins [2], but is clearly more widely distributed. The proposed biosynthetic pathway involves the dehydration/isomerization of UDP-D-GlcNAc to UDP-4-keto-6-deoxy-GlcNAc by PseB, a transamination at position 4 by PseC. The PseH protein is similar to acetyltransferases and is presumed to carry out transfer to the C-4 amine. PseH itself is occasionally missing. Often in this case, the PseG protein contains an passable acetyltransferase domain. The function of PseG when PseH is present is unknown, it may complex with PseH, or ot may be responsible for the UDP-hydrolysis that clearly must happen but is not currently assigned to an enzyme with a conserved domain for this reaction. PseI carries out the condensation with phosphoenolpyruvate to create pseudaminic acid, a reaction analagous to the carried out by NeuB in the biosynthesis of neuraminic acid (GenProp0792). PseF carries out the transfer of CMP onto pseudaminic acid to yield the most common product. In Campylobacter, the biosynthetic cluster is accompanied by the PseA protein, a homolog of WbuX and is responsible for the conversion of the N-acetyl group at position 7 into the acetimidino group. PseA is accompanied by two genes, WbuY and WbuZ which are reported to provide ammonia for the reaction (GenProp0794). Other proteins are found associated with this cluster including methylases and possible formyltransferases and deacetylases. Thus, a range of closely related structures are likely produced as mature products in various lineages.

Parent Property

GenProp0795: carbohydrate biosynthesis

Literature References

[ 1 ] Knirel YA, Kocharova NA, Shashkov AS, Dmitriev BA, Kochetkov NK, Stanislavsky ES, Mashilova GM   Somatic antigens of Pseudomonas aeruginosa. The structure of O-specific polysaccharide chains of the lipopolysaccharides from P. aeruginosa O5 (Lanyi) and immunotype 6 (Fisher).   Eur J Biochem. 1987 Mar 16;163(3):639-52.  PMID 3104041
[ 2 ] Schoenhofen IC, McNally DJ, Vinogradov E, Whitfield D, Young NM, Dick S, Wakarchuk WW, Brisson JR, Logan SM   Functional characterization of dehydratase/aminotransferase pairs from Helicobacter and Campylobacter: enzymes distinguishing the pseudaminic acid and bacillosamine biosynthetic pathways.   J Biol Chem. 2006 Jan 13;281(2):723-32. Epub 2005 Nov 11.  PMID 16286454
[ 3 ] Gryllos I, Shaw JG, Gavin R, Merino S, Tomas JM   Role of flm locus in mesophilic Aeromonas species adherence.   Infect Immun. 2001 Jan;69(1):65-74.  PMID 11119490
[ 4 ] McNally DJ, Hui JP, Aubry AJ, Mui KK, Guerry P, Brisson JR, Logan SM, Soo EC   Functional characterization of the flagellar glycosylation locus in Campylobacter jejuni 81-176 using a focused metabolomics approach.   J Biol Chem. 2006 Jul 7;281(27):18489-98. Epub 2006 May 9.  PMID 16684771

Components

Step Name	Step Num	Required	Evidence (Method)
CMP-pseudaminic acid C7-N-acetyl amidotransferase	PseA	NO	TIGR03573 (HMM-CLUST): N-acetyl sugar amidotransferase
UDP-GlcNAc C6-dehydratase/C4-reductase	PseB	YES	TIGR03589 (HMM): UDP-N-acetylglucosamine 4,6-dehydratase (inverting)
pseudaminic acid biosynthesis aminotransferase PseC	PseC	YES	TIGR03588 (HMM): UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-altrosamine transaminase
pseudaminic acid CMP-transferase	PseF	YES	TIGR03584 (HMM): pseudaminic acid cytidylyltransferase PF02348 (HMM-CLUST): cytidylyltransferase
possible pseudaminic acid biosynthesis UDP hydrolase	PseG	NO	TIGR03590 (HMM): UDP-2,4-diacetamido-2,4,6-trideoxy-beta-L-altropyranose hydrolase
possible pseudaminic acid biosynthesis N-acetyl transferase	PseH	YES	TIGR03585 (HMM): UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-altrosamine N-acetyltransferase PF00583 (HMM-CLUST): acetyltransferase, GNAT family
pseudaminic acid synthase (pyruvate condensing enzyme)	PseI	YES	TIGR03586 (HMM): pseudaminic acid synthase
pseudaminic acid biosynthesis associated methylase	PseM?	NO	TIGR03587 (HMM): pseudaminic acid biosynthesis-associated methylase
source of UDP-N-acetyl-D-glucosamine	UGlcNAc	NO	GenProp0750 (GENPROP): UDP-N-acetylglucosamine biosynthesis from fructose-6-phosphate
proteins possibly involved in pathway variants	variants	NO	MANUAL (MANUAL)

Parent Properties

Accession	Name
GenProp0795	carbohydrate biosynthesis

Sibling Properties

Accession	Name
GenProp0183	dTDP-L-rhamnose biosynthesis from dTDP-4-dehydro-L-rhamnose
GenProp0264	glucosylglycerol biosynthesis
GenProp0297	lipopolysaccharide biosynthesis
GenProp0750	UDP-N-acetylglucosamine biosynthesis from fructose-6-phosphate
GenProp0766	anhydro-N-acetylmuramic acid to N-acetylglucosamine-phosphate
GenProp0793	CMP-N-acetylneuraminate biosynthesis from UDP-N-acetylglucosamine
GenProp0794	proposed N-acetyl sugar amidation module WbuXYZ
GenProp0811	S-layer homology domain-mediated cell wall binding