2.4.1.182: lipid-A-disaccharide synthase
This is an abbreviated version!
For detailed information about lipid-A-disaccharide synthase, go to the full flat file.
Word Map on EC 2.4.1.182
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2.4.1.182
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acyltransferase
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raetz
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clockwise
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udp-glcnac
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lipopolysaccharide
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paralogue
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lps
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udp-2,3-diacylglucosamine
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castellanii
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cotranscribed
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amoebae
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micelle
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pneumophila
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bacteriol
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acanthamoeba
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glycerophospholipids
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resin
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udp-n-acetylglucosamine
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synthesis
- 2.4.1.182
- acyltransferase
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raetz
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clockwise
- udp-glcnac
- lipopolysaccharide
- paralogue
- lps
- udp-2,3-diacylglucosamine
- castellanii
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cotranscribed
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amoebae
-
micelle
- pneumophila
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bacteriol
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acanthamoeba
- glycerophospholipids
- resin
- udp-n-acetylglucosamine
- synthesis
Reaction
Synonyms
lcsC, lcsC/lpxB1, Legionella cytotoxic suppressor C, lipid A disaccharide synthase, lipid A disaccharide synthetase, LpxB, More, pgsB, synthase, lipid A disaccharide
ECTree
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Substrates Products
Substrates Products on EC 2.4.1.182 - lipid-A-disaccharide synthase
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REACTION DIAGRAM
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(1->6)-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP-2,3-diacylglucosamine + 2,3-diacylglucosamine 1-phosphate
2',3'-diacylglucosamine-(beta,1'-6)-2,3-diacylglucosamine 1-phosphate + UDP
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 3-((R)-3-hydroxytetradecanoyl)-N-acetyl-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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product analysis
?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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strong preference for 2,3-diacylated substrates, but the (R)-3-hydroxy substituent is not required
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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involved with EC 2.3.1.129 and EC 2.7.1.130 in the biosynthesis of the phosphorylated glycolipid, Lipid A, in the outer membrane of E. coli and other gram-negative bacteria
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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involved in lipid A biosynthesis
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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strong preference for 2,3-diacylated substrates, but the (R)-3-hydroxy substituent is not required
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ir
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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involved with EC 2.3.1.129 and EC 2.7.1.130 in the biosynthesis of the phosphorylated glycolipid, Lipid A, in the outer membrane of E. coli and other gram-negative bacteria
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-
?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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2,3-diacylglucosamine 1-phosphate is lipid X
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?
UDP-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 2,3-bis((R)-3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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lipid X isolated from E. coli
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?
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(1->6)-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
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?
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(1->6)-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
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?
2',3'-diacylglucosamine-(beta,1'-6)-2,3-diacylglucosamine 1-phosphate + UDP
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?
UDP-2,3-diacylglucosamine + 2,3-diacylglucosamine 1-phosphate
2',3'-diacylglucosamine-(beta,1'-6)-2,3-diacylglucosamine 1-phosphate + UDP
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?
UDP-2,3-diacylglucosamine + 2,3-diacylglucosamine 1-phosphate
2',3'-diacylglucosamine-(beta,1'-6)-2,3-diacylglucosamine 1-phosphate + UDP
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?
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
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?
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
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?
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
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?
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
UDP + 2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosaminyl 1-phosphate
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?
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 3-((R)-3-hydroxytetradecanoyl)-N-acetyl-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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0.44% of the activity with UDP-2,3-diacylglucosamine
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?
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine + 2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
UDP + 3-((R)-3-hydroxytetradecanoyl)-N-acetyl-beta-D-glucosaminyl-(1->6)-2,3-bis((R)-3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
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0.44% of the activity with UDP-2,3-diacylglucosamine
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?
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formation of lipid A disaccharide from UDP-GlcNAc and lipid X, i.e. 2,3-diacylglucosamine 1-phosphate, releasing UDP. Lipid X, i.e. 2,3-diacylglucosamine 1-phosphate, bears two R-3-hydroxymyristoyl chains in Arabidopsis thaliana and is a key precursor of lipid A. No other lipid X molecular species are detected
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additional information
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formation of lipid A disaccharide from UDP-GlcNAc and lipid X, i.e. 2,3-diacylglucosamine 1-phosphate, releasing UDP. Lipid X, i.e. 2,3-diacylglucosamine 1-phosphate, bears two R-3-hydroxymyristoyl chains in Arabidopsis thaliana and is a key precursor of lipid A. No other lipid X molecular species are detected
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additional information
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LpxB combines lipid X with the preceding lipid metabolite, UDP-2,3-bis(beta-hydroxymyristoyl)-D-glucosamine, to form lipid A disaccharide
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additional information
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LpxB only consumes lipid X in a 1:1 ratio with UDP-2,3-bis(beta-hydroxymyristoyl)-D-glucosamine. Near irreversibility of the LpxB enzyme
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additional information
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analysis of UDP binding site structure and ligand-bound structure of LpxB. The GlcNAc moiety is highly flexible or that UDP-GlcNAc is hydrolysed during soaking. The uracil base binds in a hydrophobic pocket formed by L197, P198, P231, and V233, which is on the second Rossmann-fold domain and facing the deep inter-domain cleft. The P231 carbonyl oxygen also hydrogen-bonds with N3 of uracil and the G199 amide nitrogen hydrogen-bonds with the O4 carbonyl of uracil. In addition, two water molecules connect active site residues to uracil: the first water connects the G199 carbonyl oxygen and the V233 amide nitrogen to O4 of uracil, and the second water connects the G261 amide nitrogen to the O2 carbonyl of uracil
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additional information
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analysis of UDP binding site structure and ligand-bound structure of LpxB. The GlcNAc moiety is highly flexible or that UDP-GlcNAc is hydrolysed during soaking. The uracil base binds in a hydrophobic pocket formed by L197, P198, P231, and V233, which is on the second Rossmann-fold domain and facing the deep inter-domain cleft. The P231 carbonyl oxygen also hydrogen-bonds with N3 of uracil and the G199 amide nitrogen hydrogen-bonds with the O4 carbonyl of uracil. In addition, two water molecules connect active site residues to uracil: the first water connects the G199 carbonyl oxygen and the V233 amide nitrogen to O4 of uracil, and the second water connects the G261 amide nitrogen to the O2 carbonyl of uracil
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additional information
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involved in the biosynthetic pathway leading to 3-aminoglucosamine analogues of lipid A, responsible for cytotoxic effect on the host Acanthamoeba castellanii
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additional information
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involved in the biosynthetic pathway leading to 3-aminoglucosamine analogues of lipid A, responsible for cytotoxic effect on the host Acanthamoeba castellanii
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additional information
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involved in the biosynthetic pathway leading to 3-aminoglucosamine analogues of lipid A, responsible for cytotoxic effect on the host Acanthamoeba castellanii
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additional information
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involved in the biosynthetic pathway leading to 3-aminoglucosamine analogues of lipid A, responsible for cytotoxic effect on the host Acanthamoeba castellanii
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