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Ligand 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.43

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

758653, 759062

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2.4.2.43

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

739106, 738342, 739657, 739708

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2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A) = lipid II(A) + undecaprenyl phosphate

698718

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2.4.2.43

3 entries

2.4.2.B4

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-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 + 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-alpha-D-glucopyranose + undecaprenyl phosphate

698718

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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.B13

4-deoxy-4-formamido-beta-L-arabinopyranosyl undecaprenyl phosphate + H2O = 4-amino-4-deoxy-alpha-L-arabinose-undecaprenyl phosphate + formate

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Substrate in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.43

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

758653, 759062

-

2.4.2.43

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

739106, 738342, 739657, 739708

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2.4.2.43

4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate + lipid IV(A) = lipid II(A) + undecaprenyl phosphate

698718

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2.4.2.43

3 entries

2.4.2.B4

3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-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 + 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate = 3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->4)-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-[[(3R)-3-hydroxypentadecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-(4-amino-4-deoxy-alpha-L-arabinopyranosyl)phosphono-alpha-D-glucopyranose + undecaprenyl phosphate

698718

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Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.B13

4-deoxy-4-formamido-beta-L-arabinopyranosyl undecaprenyl phosphate + H2O = 4-amino-4-deoxy-alpha-L-arabinose-undecaprenyl phosphate + formate

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Enzyme Kinetic Parameters

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

698718

11535604

An inner membrane enzyme in Salmonella and Escherichia coli that transfers 4-amino-4-deoxy-L-arabinose to lipid A: induction on polymyxin-resistant mutants and role of a novel lipid-linked donor

2001

Trent, M.S.; Ribeiro, A.A.; Lin, S.; Cotter, R.J.; Raetz, C.R.

J. Biol. Chem.

276

43122-43131

738342

26515403

ArnT proteins that catalyze the glycosylation of lipopolysaccharide share common features with bacterial N-oligosaccharyltransferases

2016

Tavares-Carreon, F.; Fathy Mohamed, Y.; Andrade, A.; Valvano, M.A.

Glycobiology

26

286-300

739106

25846400

Extracellular zinc induces phosphoethanolamine addition to Pseudomonas aeruginosa lipid A via the ColRS two-component system

2015

Nowicki, E.M.; OBrien, J.P.; Brodbelt, J.S.; Trent, M.S.

Mol. Microbiol.

97

166-178

739657

26030265

Burkholderia cenocepacia and Salmonella enterica ArnT proteins that transfer 4-amino-4-deoxy-l-arabinose to lipopolysaccharide share membrane topology and functional amino acids

2015

Tavares-Carreon, F.; Patel, K.B.; Valvano, M.A.

Sci. Rep.

5

10773

739708

26912703

Structures of aminoarabinose transferase ArnT suggest a molecular basis for lipid A glycosylation.

2016

Petrou, V.; Herrera, C.; Schultz, K.; Clarke, O.; Vendome, J.; Tomasek, D.; Banerjee, S.; Rajashankar, K.; Dufrisne, M.; Kloss, B.; Kloppmann, E.; Rost, B.; Klug, C.; Trent, M.; Shapiro, L.; Mancia, F.

Science

351

608-612

758653

29914952

Contribution of novel amino acid alterations in PmrA or PmrB to colistin resistance in mcr-negative Escherichia coli clinical isolates, including major multidrug-resistant lineages O25b H4-ST131-H30Rx and Non-x

2018

Sato, T.; Shiraishi, T.; Hiyama, Y.; Honda, H.; Shinagawa, M.; Usui, M.; Kuronuma, K.; Masumori, N.; Takahashi, S.; Tamura, Y.; Yokota, S.I.

Antimicrob. Agents Chemother.

62

e00864-18

759062

31233657

Synthetic phosphodiester-linked 4-amino-4-deoxy-L-arabinose derivatives demonstrate that ArnT is an inverting aminoarabinosyl transferase

2019

Olagnon, C.; Monjaras Feria, J.; Gruenwald-Gruber, C.; Blaukopf, M.; Valvano, M.A.; Kosma, P.

Chembiochem

20

2936-2948

Links to other databases for 4-amino-4-deoxy-alpha-L-arabinopyranosyl undecaprenyl phosphate

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ChEBI

PubChem