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IUBMB CommentsThe enzyme is found in bacterial species whose lipid A contains 2,3-diamino-2,3-dideoxy-D-glucopyranose. Some enzymes, such as that from Leptospira interrogans, are highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose, while others, such as the enzyme from Acidithiobacillus ferrooxidans, are also able to accept UDP-N-acetyl-alpha-D-glucosamine (cf. EC 2.3.1.129, acyl-[acyl-carrier-protein]---UDP-N-acetylglucosamine O-acyltransferase). The enzymes from different organisms also differ in their specificity for the acyl donor. The enzyme from Leptospira interrogans is highly specific for (3R)-3-hydroxydodecanoyl-[acp], while that from Mesorhizobium loti functions almost equally well with 10-, 12-, and 14-carbon 3-hydroxyacyl-[acp]s.
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(3R)-3-hydroxyacyl-[acyl-carrier-protein]:UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose 3-N-[(3R)-hydroxyacyl]transferase
The enzyme is found in bacterial species whose lipid A contains 2,3-diamino-2,3-dideoxy-D-glucopyranose. Some enzymes, such as that from Leptospira interrogans, are highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose, while others, such as the enzyme from Acidithiobacillus ferrooxidans, are also able to accept UDP-N-acetyl-alpha-D-glucosamine (cf. EC 2.3.1.129, acyl-[acyl-carrier-protein]---UDP-N-acetylglucosamine O-acyltransferase). The enzymes from different organisms also differ in their specificity for the acyl donor. The enzyme from Leptospira interrogans is highly specific for (3R)-3-hydroxydodecanoyl-[acp], while that from Mesorhizobium loti functions almost equally well with 10-, 12-, and 14-carbon 3-hydroxyacyl-[acp]s.
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
additional information
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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additional information

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enzyme is also able to accept UDP-N-acetyl-alpha-D-glucosamine, cf. EC 2.3.1.129 and displays relaxed acyl donor chain length selectivity
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additional information
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poor substrates: (3R)-3-hydroxydecanoyl-[acyl-carrier protein], 3-hydroxypalmitoyl-[acyl-carrier protein], (3R)-3-hydroxymyristoyl-[acyl-carrier protein]. Enzyme is highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose
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additional information
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poor substrates: (3R)-3-hydroxydecanoyl-[acyl-carrier protein], 3-hydroxypalmitoyl-[acyl-carrier protein], (3R)-3-hydroxymyristoyl-[acyl-carrier protein]. Enzyme is highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose
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additional information
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poor substrate: 3-hydroxypalmitoyl-[acyl-carrier protein]
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additional information
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poor substrate: 3-hydroxypalmitoyl-[acyl-carrier protein]
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
additional information
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxydecanoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxydecanoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxylauroyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxylauroyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose

acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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(3R)-3-hydroxymyristoyl-[acyl-carrier protein] + UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucopyranose
acyl-carrier protein + UDP-2-acetamido-2,3-dideoxy-3-[[(3R)-3-hydroxymyristoyl]amino]-alpha-D-glucopyranose
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additional information

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enzyme is also able to accept UDP-N-acetyl-alpha-D-glucosamine, cf. EC 2.3.1.129 and displays relaxed acyl donor chain length selectivity
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additional information
?
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poor substrates: (3R)-3-hydroxydecanoyl-[acyl-carrier protein], 3-hydroxypalmitoyl-[acyl-carrier protein], (3R)-3-hydroxymyristoyl-[acyl-carrier protein]. Enzyme is highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose
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additional information
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poor substrates: (3R)-3-hydroxydecanoyl-[acyl-carrier protein], 3-hydroxypalmitoyl-[acyl-carrier protein], (3R)-3-hydroxymyristoyl-[acyl-carrier protein]. Enzyme is highly specific for 2,3-diamino-2,3-dideoxy-D-glucopyranose
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additional information
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poor substrate: 3-hydroxypalmitoyl-[acyl-carrier protein]
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additional information
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poor substrate: 3-hydroxypalmitoyl-[acyl-carrier protein]
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.0005
substrate (3R)-3-hydroxypalmitoyl-[acyl-carrier protein], pH 8, 30°C
0.00052
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substrate (3R)-3-hydroxydecanoyl-[acyl-carrier protein], pH 8, 30°C
0.0006
substrate (3R)-3-hydroxydecanoyl-[acyl-carrier protein], pH 8, 30°C
0.0008
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substrate (3R)-3-hydroxylauroyl-[acyl-carrier protein], pH 8, 30°C
0.00081
substrate (3R)-3-hydroxylauroyl-[acyl-carrier protein], pH 8, 30°C
0.0014
substrate (3R)-3-hydroxylauroyl-[acyl-carrier protein], pH 8, 30°C
0.002
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substrate (3R)-3-hydroxymyristoyl-[acyl-carrier protein], pH 8, 30°C
0.0034
substrate (3R)-3-hydroxymyristoyl-[acyl-carrier protein], pH 8, 30°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
metabolism
enzyme is also able to accept UDP-N-acetyl-alpha-D-glucosamine, cf. EC 2.3.1.129 and displays relaxed acyl donor chain length selectivity
physiological function

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this LpxA acyltransferase requires an UDP-GlcNAc derivative in which an amine replaces the glucosamine 3-OH group. The enzyme from Mesorhizobium loti functions almost equally well with 10-, 12-, and 14-carbon 3-hydroxyacyl-[ACP]s. Acylation takes place on the nitrogen atom of UDP-GlcNAc3N at the pyranose 3-position
physiological function
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this LpxA acyltransferase requires an UDP-GlcNAc derivative in which an amine replaces the glucosamine 3-OH group. The enzyme from Mesorhizobium loti functions almost equally well with 10-, 12-, and 14-carbon 3-hydroxyacyl-[ACP]s. Acylation takes place on the nitrogen atom of UDP-GlcNAc3N at the pyranose 3-position
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Robins, L.; Williams, A.; Raetz, C.
Structural basis for the sugar nucleotide and acyl-chain selectivity of Leptospira interrogans LpxA
Biochemistry
48
6191-6201
2009
Leptospira interrogans serogroup Icterohaemorrhagiae serovar Lai IPAV (Q8EZA6), Leptospira interrogans serogroup Icterohaemorrhagiae serovar Lai IPAV 56601 (Q8EZA6)
brenda
Sweet, C.; Williams, A.; Karbarz, M.; Werts, C.; Kalb, S.; Cotter, R.; Raetz, C.
Enzymatic synthesis of lipid A molecules with four amide-linked acyl chains LpxA acyltransferases selective for an analog of UDP-N-acetylglucosamine in which an amine replaces the 3''-hydroxyl group
J. Biol. Chem.
279
25411-25419
2004
Mesorhizobium loti, Acidithiobacillus ferrooxidans (Q6QHI7), Leptospira interrogans serogroup Icterohaemorrhagiae serovar Lai IPAV (Q8EZA6), Mesorhizobium loti ATCC 700743, Leptospira interrogans serogroup Icterohaemorrhagiae serovar Lai IPAV 56601 (Q8EZA6)
brenda