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Enzyme Nomenclature
Information on EC 2.4.2.43 - lipid IVA 4-amino-4-deoxy-L-arabinosyltransferase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
2.4.2.43
-
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RECOMMENDED NAME
GeneOntology No.
lipid IVA 4-amino-4-deoxy-L-arabinosyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A = alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA = 4'-alpha-L-Ara4N-alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + lipid IVA = lipid IIA + ditrans,octacis-undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + lipid IVA = lipid IIA + ditrans,octacis-undecaprenyl phosphate
lipid IV(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose. Lipid II(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-alpha-D-glucopyranose
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4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + lipid IVA = lipid IIA + ditrans,octacis-undecaprenyl phosphate
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
4-amino-4-deoxy-alpha-L-2-aminoarabinopyranosyl ditrans,octacis-undecaprenyl phosphate:lipid IVA L-2-aminoarabinopyranosyltransferase
Integral membrane protein present in the inner membrane of certain Gram negative endobacteria. In strains that do not produce 3-deoxy-D-manno-octulosonic acid (Kdo), the enzyme adds a single arabinose unit to the 1-phosphate moiety of the tetra-acylated lipid A precursor, lipid IVA. In the presence of a Kdo disaccharide, the enzyme primarily adds an arabinose unit to the 4-phosphate of lipid A molecules. The Salmonella typhimurium enzyme can add arabinose units to both positions.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
physiological function
malfunction
LpxT-dependent lipid A modification is not restored in arnT or eptA mutants
malfunction
-
LpxT-dependent lipid A modification is not restored in arnT or eptA mutants
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physiological function
-
ArnT confers resistance to the antibiotic polymyxin in Salmonella typhimurium and Escherichia coli through the modification of lipid A, a major component of the outer surface of Gram-negative bacteria. ArnT transfers a neutral aminoarabinose moiety onto the negative phosphate groups of lipid A, reducing the surface charge of the bacteria and preventing cationic peptides such as polymyxin from electrostatically recognizing and killing the bacteria. Only small amounts of ArnT are necessary to provide resistance against polymyxin to the bacterial cell
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A)
lipid II(A) + undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
the reaction is part of a enzymatic pathway by which Gram-negative bacteria acquire antibiotic resistance
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
ArnT confers resistance to the antibiotic polymyxin in Salmonella typhimurium and Escherichia coli through the modification of lipid A, a major component of the outer surface of Gram-negative bacteria. ArnT transfers a neutral aminoarabinose moiety onto the negative phosphate groups of lipid A, reducing the surface charge of the bacteria and preventing cationic peptides such as polymyxin from electrostatically recognizing and killing the bacteria. Only small amounts of ArnT are necessary to provide resistance against polymyxin to the bacterial cell
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
the reaction is part of a enzymatic pathway by which Gram-negative bacteria acquire antibiotic resistance
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A)
lipid II(A) + undecaprenyl phosphate
-
ArnT adds a single 4-amino-4-deoxy-alpha-L-arabinose unit to the 1-phosphate moiety of the tetraacylated lipid A precursor, lipid IV(A), which lacks Kdo and forms lipid II (A). Transfer to lipid A occurs on the periplasmic side of the inner membrane. ArnT is a bifunctional glycosyltransferase in that it can incorporate two 4-amino-4-deoxy-alpha-L-arabinose units. Lipid IV(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose. Lipid II(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-alpha-D-glucopyranose
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A)
lipid II(A) + undecaprenyl phosphate
-
ArnT adds a single 4-amino-4-deoxy-alpha-L-arabinose unit to the 1-phosphate moiety of the tetraacylated lipid A precursor. Lipid IV(A), which lacks Kdo and forms lipid II (A)lipid IV(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose. Lipid II(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-alpha-D-glucopyranose
-
-
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A)
lipid II(A) + undecaprenyl phosphate
-
ArnT adds a single 4-amino-4-deoxy-alpha-L-arabinose unit to the 1-phosphate moiety of the tetraacylated lipid A precursor, lipid IV(A), which lacks Kdo and forms lipid II (A). Transfer to lipid A occurs on the periplasmic side of the inner membrane. ArnT is a bifunctional glycosyltransferase in that it can incorporate two 4-amino-4-deoxy-alpha-L-arabinose units. Lipid IV(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose. Lipid II(A) = 2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-alpha-D-glucopyranose
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
the reaction is part of a enzymatic pathway by which Gram-negative bacteria acquire antibiotic resistance
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
O52327
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
ArnT confers resistance to the antibiotic polymyxin in Salmonella typhimurium and Escherichia coli through the modification of lipid A, a major component of the outer surface of Gram-negative bacteria. ArnT transfers a neutral aminoarabinose moiety onto the negative phosphate groups of lipid A, reducing the surface charge of the bacteria and preventing cationic peptides such as polymyxin from electrostatically recognizing and killing the bacteria. Only small amounts of ArnT are necessary to provide resistance against polymyxin to the bacterial cell
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,poly-cis-undecaprenyl phosphate + lipid IVA
lipid IIA + di-trans,poly-cis-undecaprenyl phosphate
-
the reaction is part of a enzymatic pathway by which Gram-negative bacteria acquire antibiotic resistance
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid A
alpha-Kdo-(2->4)-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + ditrans,octacis-undecaprenyl phosphate
-
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Triton X-100
-
transferase�transfer of the 4-amino-4-deoxy-alpha-L-arabinose unit from its putative isoprenoid carrier, undecaprenyl phosphate-4-amino-4-deoxy-alpha-L-arabinose, to the radiolabeled acceptor [4'-32P]lipid IV(A) is dependent upon the presence of the nonionic detergent Triton X-100, with maximal activity observed at 0.2% in the assay system
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Cupriavidus metallidurans (strain ATCC 43123 / DSM 2839 / NBRC 102507 / CH34)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
the secondary structure of ArnT is not dependent on disulfide bridges, Salmonella typhimurium ArnT contains no disulfide bonds
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purifiation of 6*His-tagged ArnT. HisLink nickel affinity chromatography coupled with anion exchange chromatography results in the best overall purifiation strategy for dodecylmaltoside-solubilized ArnT
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overxpression of the L-Ara4N lipid A transferase (ArnT) behind a T7lac promoter
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the 6*His-tagged ArnT gene-encoded plasmids are transformed into Escherichia coli NovaBlue (Novagen) cells for protein expression. The gene is knocked out of the chromosomal DNA of BL21 (BL21(DE3)DELTAArnT), leaving the plasmid-encoded ArnT to be the only ArnT expressed in the system
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E84A
C148A/C149A/C173S/C216S/C318S/C383S/C400S/C411S
-
when assayed for growth in the presence of polymyxin, the cysteine-free construct of ArnT supports growth at a level similar to that of the native protein
C148S/C149S/C173S/C216S/C318S/C383S/C400S/C411S
-
mutant enzyme is inactive
C173S/C216S/C318S/C383S/C400S/C411S
-
when assayed for growth in the presence of polymyxin, the cysteine-free construct of ArnT supports growth at 70% of the native protein
additional information
-
analysis of 31 point mutations within a putative periplasmic loop of the cysteine-free ArnT protein, carried out using an in vivo growth assay coupled with expression studies, identification of the first time specific critical residues within the bacterial transferase. These critical residues fall into two categories: those that disrupt initial protein folding or membrane localization and those that fail to confer in vivo resistance to polymyxin despite being expressed to the inner membrane
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LINKS TO OTHER DATABASES (specific for EC-Number 2.4.2.43)
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