Information on EC 2.7.7.92 - 3-deoxy-D-glycero-D-galacto-nonulopyranosonate cytidylyltransferase

for references in articles please use BRENDA:EC2.7.7.92
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.7.7.92
-
RECOMMENDED NAME
GeneOntology No.
3-deoxy-D-glycero-D-galacto-nonulopyranosonate cytidylyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CTP + 3-deoxy-D-glycero-D-galacto-nononate = diphosphate + CMP-3-deoxy-D-glycero-D-galacto-nononate
show the reaction diagram
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
CMP-2-keto-3-deoxy-D-glycero-D-galacto-nononate biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
CTP:3-deoxy-D-glycero-D-galacto-nononate cytidylyltransferase
The enzyme is part of the biosynthesis pathway of the sialic acid 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonate (Kdn). Kdn is abundant in extracellular glycoconjugates of lower vertebrates such as fish and amphibians, but is also found in the capsular polysaccharides of bacteria that belong to the Bacteroides genus.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cf. EC 2.7.7.43
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
CTP + 3,5-dideoxy-5-fluoro-D-glycero-D-galacto-nonulosonic acid
diphosphate + CMP-3,5-dideoxy-5-fluoro-D-glycero-D-galacto-nononate
show the reaction diagram
-
-
12% conversion within 3 h
-
?
CTP + 3-deoxy-D-glycero-D-galacto-nononate
diphosphate + CMP-3-deoxy-D-glycero-D-galacto-nononate
show the reaction diagram
CTP + 5-bromo-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid
diphosphate + CMP-5-bromo-3,5-dideoxy-D-glycero-D-galacto-nononate
show the reaction diagram
-
-
29% conversion within 3 h
-
?
CTP + 5-chloro-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid
diphosphate + CMP-5-chloro-3,5-dideoxy-D-glycero-D-galacto-nononate
show the reaction diagram
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-
25% conversion within 3 h
-
?
CTP + 5-N-fluoroacetylneuraminic acid
diphosphate + CMP-5-N-fluoroacetylneuraminic acid
show the reaction diagram
-
-
21% conversion within 3 h
-
?
CTP + N-acetylneuraminic acid
diphosphate + CMP-N-acetylneuraminic acid
show the reaction diagram
CTP + N-glycolylneuraminic acid
diphosphate + CMP-N-glycolylneuraminic acid
show the reaction diagram
-
-
-
-
?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
CTP + 3-deoxy-D-glycero-D-galacto-nononate
diphosphate + CMP-3-deoxy-D-glycero-D-galacto-nononate
show the reaction diagram
-
preferred substrate
-
-
?
CTP + N-acetylneuraminic acid
diphosphate + CMP-N-acetylneuraminic acid
show the reaction diagram
-
-
-
-
?
CTP + N-glycolylneuraminic acid
diphosphate + CMP-N-glycolylneuraminic acid
show the reaction diagram
-
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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or Mn 2+, required. 25 mg2+ stimulates reaction with 3-deoxy-D-glycero-D-galacto-nononate more than 10fold
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.7
3,5-dideoxy-5-fluoro-D-glycero-D-galacto-nonulosonic acid
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pH 9.0, 25°C
0.56 - 3.3
3-deoxy-D-glycero-D-galacto-nononate
0.4
5-bromo-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid
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pH 9.0, 25°C
0.53
5-chloro-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid
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pH 9.0, 25°C
0.51 - 2.7
CTP
0.26 - 7.6
N-acetylneuraminic acid
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.02
CTP
pH 7.5, 25°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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expression of CMP-KDN synthetase is temporally correlated with development and parallels the developmental expression of (KDN)GM3 in sperm
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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the crucial nuclear localization signal in the fish enzyme is bipartite and the functionality depends on a free N-terminus. Nuclear transport and enzymatic activity are independent functions. The sequence K5K6R7 is sufficient to direct GFP to the nucleus, and is necessary for the nuclear import of the CMP-Sia-synthetase in fish cells
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
66000
SDS-PAGE, recombinant thioredoxin fusion protein
69000
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SDS-PAGE, recombinant thioredoxin fusion protein
260000
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gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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construction of mutants lacking individual basic amino acids in the N-terminus, disruption of putative nuclear localization signal