N,N'-diacetylchitobiose phosphorylase

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N,N'-diacetylchitobiose phosphorylase
Identifiers
EC no. 2.4.1.280
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N,N'-diacetylchitobiose phosphorylase (EC 2.4.1.280, chbP (gene)) is an enzyme with the systematic name N,N'-diacetylchitobiose:phosphate N-acetyl-D-glucosaminyltransferase. [1] [2] [3] This enzyme was found in the genus Vibrio initially but has now been found to be taken up by Escherichia coli as well as many other bacteria. One study shows that Escherichia coli can replicate on a medium that is just composed of GlcNAc a product of phosphorylation of N,N'-diacetylchitobiose as the sole source of carbon. Because E. coli can go on this medium, the enzyme is present. The enzyme has also been found in multiple eukaryotic cells as well, especially in eukaryotes that make chitin and break chitin down. It is believed that N,N'-diacetylchitobiose phosphorylase is an integral part of the phosphoenolpyruvate:glucose phosphotransferase system (PTS). It is assumed that it is involved with Enzyme Complex II of the PTS and is involved with the synthesis of chitin. [4] The enzyme is specific for N,N'-diacetylchitobiose.

Mechanism

This enzyme catalyses the following chemical reaction

N,N'-diacetylchitobiose + phosphate N-acetyl-D-glucosamine + N-acetyl-alpha-D-glucosamine 1-phosphate

The mechanism for this reaction is as follows the enzymatic phosphorolysis of N,N’-diacetylchitobiose phosphorylase begins with the direct nucleophilic attack to the glycosidic bond with the aid of D492 or aspartic acid residue 492 of the active site of the enzyme, which donates a proton to the glycosidic oxygen atom, and then proceeds through an oxocarbenium cation activated by ion-like transition state. [1]

Related Research Articles

PEP group translocation, also known as the phosphotransferase system or PTS, is a distinct method used by bacteria for sugar uptake where the source of energy is from phosphoenolpyruvate (PEP). It is known to be a multicomponent system that always involves enzymes of the plasma membrane and those in the cytoplasm.

In enzymology, a phosphoglucosamine mutase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UDP-N-acetylglucosamine 2-epimerase</span> Class of enzymes

In enzymology, an UDP-N-acetylglucosamine 2-epimerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Glucosamine-6-phosphate deaminase</span>

In enzymology, a glucosamine-6-phosphate deaminase (EC 3.5.99.6) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">N-acetylglucosamine-6-phosphate deacetylase</span>

In enzymology, N-acetylglucosamine-6-phosphate deacetylase (EC 3.5.1.25), also known as GlcNAc-6-phosphate deacetylase or NagA, is an enzyme that catalyzes the deacetylation of N-acetylglucosamine-6-phosphate (GlcNAc-6-P) to glucosamine-6-phosphate (GlcN-6-P):

In enzymology, a glucosamine-1-phosphate N-acetyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Glucosamine-phosphate N-acetyltransferase</span>

In enzymology, glucosamine-phosphate N-acetyltransferase (GNA) is an enzyme that catalyzes the transfer of an acetyl group from acetyl-CoA to the primary amine in glucosamide-6-phosphate, generating a free CoA and N-acetyl-D-glucosamine-6-phosphate.

<span class="mw-page-title-main">UDP-N-acetylglucosamine 1-carboxyvinyltransferase</span> Class of enzymes

In enzymology, an UDP-N-acetylglucosamine 1-carboxyvinyltransferase is an enzyme that catalyzes the first committed step in peptidoglycan biosynthesis of bacteria:

In enzymology, a 1,3-beta-galactosyl-N-acetylhexosamine phosphorylase is an enzyme that catalyzes the chemical reaction

In enzymology, a [3-methyl-2-oxobutanoate dehydrogenase (acetyl-transferring)] is an enzyme that catalyzes the chemical reaction

In enzymology, an acetylglutamate kinase is an enzyme that catalyzes the chemical reaction:

<span class="mw-page-title-main">N-acetylglucosamine kinase</span>

In enzymology, a N-acetylglucosamine kinase is an enzyme that catalyzes the chemical reaction

In enzymology, a protein-Npi-phosphohistidine-sugar phosphotransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Phosphocarrier protein</span>

Histidine-containing phosphocarrier protein (HPr) is a small cytoplasmic protein that is a component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS).

UDP-N-acetylglucosamine kinase is an enzyme with systematic name ATP:UDP-N-acetyl-alpha-D-glucosamine 3'-phosphotransferase. This enzyme catalyses the following chemical reaction

UDP-N-acetylglucosamine—undecaprenyl-phosphate N-acetylglucosaminephosphotransferase is an enzyme with systematic name UDP-N-acetyl-alpha-D-glucosamine:ditrans,octacis-undecaprenyl phosphate N-acetyl-alpha-D-glucosaminephosphotransferase. This enzyme catalyses the following chemical reaction

UDP-N-acetylglucosamine 2-epimerase (hydrolysing) (EC 3.2.1.183, UDP-N-acetylglucosamine 2-epimerase, GNE (gene), siaA (gene), neuC (gene)) is an enzyme with systematic name UDP-N-acetyl-alpha-D-glucosamine hydrolase (2-epimerising). This enzyme catalyses the following chemical reaction

UDP-2,3-diacylglucosamine diphosphatase (EC 3.6.1.54, UDP-2,3-diacylglucosamine hydrolase, UDP-2,3-diacylglucosamine pyrophosphatase, ybbF (gene), lpxH (gene)) is an enzyme with systematic name UDP-2,3-bis((3R)-3-hydroxymyristoyl)-alpha-D-glucosamine 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate phosphohydrolase. This enzyme catalyses the following chemical reaction

N-acetylmuramic acid 6-phosphate etherase (EC 4.2.1.126, MurNAc-6-P etherase, MurQ) is an enzyme with systematic name (R)-lactate hydro-lyase (adding N-acetyl-D-glucosamine 6-phosphate; N-acetylmuramate 6-phosphate-forming). This enzyme catalyses the following chemical reaction

The PTS Lactose-N,N’-Diacetylchitobiose (Lac) Family includes several sequenced lactose porters of Gram-positive bacteria, as well as the Escherichia coli and Borrelia burgdorferi N,N'-diacetylchitobiose (Chb) porters. It is part of the PTS-GFL superfamily. The former can transport aromatic β-glucosides and cellobiose, as well as Chb. However, only Chb induces expression of the chb operon.

References

  1. 1 2 Park JK, Keyhani NO, Roseman S (October 2000). "Chitin catabolism in the marine bacterium Vibrio furnissii. Identification, molecular cloning, and characterization of A N, N'-diacetylchitobiose phosphorylase". The Journal of Biological Chemistry. 275 (42): 33077–83. doi: 10.1074/jbc.m001042200 . PMID   10913116.
  2. Honda Y, Kitaoka M, Hayashi K (January 2004). "Reaction mechanism of chitobiose phosphorylase from Vibrio proteolyticus: identification of family 36 glycosyltransferase in Vibrio". The Biochemical Journal. 377 (Pt 1): 225–32. doi:10.1042/bj20031171. PMC   1223840 . PMID   13678418.
  3. Hidaka M, Honda Y, Kitaoka M, Nirasawa S, Hayashi K, Wakagi T, Shoun H, Fushinobu S (June 2004). "Chitobiose phosphorylase from Vibrio proteolyticus, a member of glycosyl transferase family 36, has a clan GH-L-like (alpha/alpha)(6) barrel fold". Structure. 12 (6): 937–47. doi: 10.1016/j.str.2004.03.027 . PMID   15274915.
  4. Keyhani NO, Wang LX, Lee YC, Roseman S (October 2000). "The chitin disaccharide, N,N'-diacetylchitobiose, is catabolized by Escherichia coli and is transported/phosphorylated by the phosphoenolpyruvate:glycose phosphotransferase system". The Journal of Biological Chemistry. 275 (42): 33084–90. doi: 10.1074/jbc.M001043200 . PMID   10913117.