3.5.1.108: UDP-3-O-acyl-N-acetylglucosamine deacetylase

This is an abbreviated version!
For detailed information about UDP-3-O-acyl-N-acetylglucosamine deacetylase, go to the full flat file.

Reaction

Synonyms

deacetylase, deacetylase LpxC, DHTase, EnvA protein, LpxC, LpxC deacetylase, LpxC enzyme, LpxC protein, UDP-(3-O-(R-3-hydroxymyristoyl))-N-acetylglucosamine deacetylase, UDP-(3-O-acyl)-N-acetylglucosamine deacetylase, UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, UDP-3-O-(acyl)-N-acetylglucosamine deacetylase, UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase, UDP-3-O-(R-3-hydroxymyristoyl)-GlcNAc deacetylase, UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, UDP-3-O-(R-3-hydroxymyristoyl)-Nacetylglucosamine deacetylase, UDP-3-O-acyl-GlcNAc deacetylase, UDP-3-O-acyl-N-acetylglucosamine deacetylase, UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetylglucosamine amidohydrolase, UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase, UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase, UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase enzyme, uridine diphosphate-(3-O-(R-3-hydroxymyristoyl))-N-acetylglucosamine deacetylase, zinc deacetylase LpxC

ECTree

     3 Hydrolases

         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds

             3.5.1 In linear amides

                3.5.1.108 UDP-3-O-acyl-N-acetylglucosamine deacetylase

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Results	in table
1	Activating Compound
23088	AA Sequence
19	Application
1	CAS Registry Number
16	Cloned(Commentary)
11	Crystallization (Commentary)
20	General Information
2	General Stability
501	IC50 Value
808	Inhibitors
24	kcat/KM [mM/s]
57	Ki Value [mM]
21	KM Value [mM]
1	Localization
37	Metals/Ions
5	Molecular Weight [Da]
36	Natural Substrates/ Products (Substrates)
96	Organism
11	Pathway
65	PDB ID
18	pH Optimum
2	pH Range
77	Protein Variants
25	Purification (Commentary)
1	Reaction
71	Reference
4	Specific Activity [micromol/min/mg]
86	Substrates and Products (Substrate)
4	Subunits
123	Synonyms
1	Systematic Name
16	Temperature Optimum [°C]
2	Temperature Stability [°C]
22	Turnover Number [1/s]

Reference

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Reference on EC 3.5.1.108 - UDP-3-O-acyl-N-acetylglucosamine deacetylase

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

486257

Sorensen, P.G.; Lutkenhaus, J.; Young, K.; Eveland, S.S.; Anderson, M.S.; Raetz, C.R.H.

Regulation of UDP-3-O-[R-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase in Escherichia coli. The second enzymic step of lipid A biosynthesis

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271

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1996

Escherichia coli

8824222

brenda

681452

Fuehrer, F.; Mueller, A.; Baumann, H.; Langklotz, S.; Kutscher, B.; Narberhaus, F.

Sequence and length recognition of the C-terminal turnover element of LpxC, a soluble substrate of the membrane-bound FtsH protease

J. Mol. Biol.

372

485-496

2007

Escherichia coli

17651755

brenda

681983

Fuehrer, F.; Langklotz, S.; Narberhaus, F.

The C-terminal end of LpxC is required for degradation by the FtsH protease

Mol. Microbiol.

59

1025-1036

2006

Escherichia coli

16420369

brenda

695335

Buetow, L.; Dawson, A.; Hunter, W.N.

The nucleotide-binding site of Aquifex aeolicus LpxC

Acta Crystallogr. Sect. F

62

1082-1086

2006

Aquifex aeolicus (O67648), Aquifex aeolicus

17077484

brenda

695538

Wang, W.; Maniar, M.; Jain, R.; Jacobs, J.; Trias, J.; Yuan, Z.

A fluorescence-based homogeneous assay for measuring activity of UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase

Anal. Biochem.

290

338-346

2001

Escherichia coli

11237337

brenda

695628

Clements, J.M.; Coignard, F.; Johnson, I.; Chandler, S.; Palan, S.; Waller, A.; Wijkmans, J.; Hunter, M.G.

Antibacterial activities and characterization of novel inhibitors of LpxC

Antimicrob. Agents Chemother.

46

1793-1799

2002

Escherichia coli, Escherichia coli D22

12019092

brenda

695629

Mdluli, K.E.; Witte, P.R.; Kline, T.; Barb, A.W.; Erwin, A.L.; Mansfield, B.E.; McClerren, A.L.; Pirrung, M.C.; Tumey, L.N.; Warrener, P.; Raetz, C.R.; Stover, C.K.

Molecular validation of LpxC as an antibacterial drug target in Pseudomonas aeruginosa

Antimicrob. Agents Chemother.

50

2178-2184

2006

Escherichia coli, Pseudomonas aeruginosa

16723580

brenda

696180

Anderson, M.S.; Robertson, A.D.; Macher, I.; Raetz, C.R.

Biosynthesis of lipid A in Escherichia coli: identification of UDP-3-O-[(R)-3-hydroxymyristoyl]-alpha-D-glucosamine as a precursor of UDP-N2,O3-bis[(R)-3-hydroxymyristoyl]-alpha-D-glucosamine

Biochemistry

27

1908-1917

1988

Escherichia coli

3288280

brenda

696193

Jackman, J.E.; Raetz, C.R.; Fierke, C.A.

UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase of Escherichia coli is a zinc metalloenzyme

Biochemistry

38

1902-1911

1999

Escherichia coli

10026271

brenda

696198

Jackman, J.E.; Raetz, C.R.; Fierke, C.A.

Site-directed mutagenesis of the bacterial metalloamidase UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Identification of the zinc binding site

Biochemistry

40

514-523

2001

Aquifex aeolicus, Escherichia coli

11148046

brenda

696204

Coggins, B.E.; McClerren, A.L.; Jiang, L.; Li, X.; Rudolph, J.; Hindsgaul, O.; Raetz, C.R.; Zhou, P.

Refined solution structure of the LpxC-TU-514 complex and pKa analysis of an active site histidine: insights into the mechanism and inhibitor design

Biochemistry

44

1114-1126

2005

Aquifex aeolicus (O67648), Aquifex aeolicus

15667205

brenda

696206

McClerren, A.L.; Endsley, S.; Bowman, J.L.; Andersen, N.H.; Guan, Z.; Rudolph, J.; Raetz, C.R.

A slow, tight-binding inhibitor of the zinc-dependent deacetylase LpxC of lipid A biosynthesis with antibiotic activity comparable to ciprofloxacin

Biochemistry

44

16574-16583

2005

Aquifex aeolicus, Escherichia coli, Escherichia coli R477

16342948

brenda

696209

Hernick, M.; Fierke, C.A.

Molecular recognition by Escherichia coli UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase is modulated by bound metal ions

Biochemistry

45

14573-14581

2006

Escherichia coli

17144651

brenda

696210

Hernick, M.; Fierke, C.A.

Catalytic mechanism and molecular recognition of E. coli UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase probed by mutagenesis

Biochemistry

45

15240-15248

2006

Escherichia coli

17176046

brenda

696211

Gennadios, H.A.; Whittington, D.A.; Li, X.; Fierke, C.A.; Christianson, D.W.

Mechanistic inferences from the binding of ligands to LpxC, a metal-dependent deacetylase

Biochemistry

45

7940-7948

2006

Aquifex aeolicus (O67648)

16800620

brenda

696322

Barb, A.W.; Leavy, T.M.; Robins, L.I.; Guan, Z.; Six, D.A.; Zhou, P.; Hangauer, M.J.; Bertozzi, C.R.; Raetz, C.R.

Uridine-based inhibitors as new leads for antibiotics targeting Escherichia coli LpxC

Biochemistry

48

3068-3077

2009

Escherichia coli, Helicobacter pylori, Rhizobium leguminosarum

19256534

brenda

696606

Kadam, R.U.; Roy, N.

Cluster analysis and two-dimensional quantitative structure-activity relationship (2D-QSAR) of Pseudomonas aeruginosa deacetylase LpxC inhibitors

Bioorg. Med. Chem. Lett.

16

5136-5143

2006

Pseudomonas aeruginosa

16879960

brenda

696607

Kadam, R.U.; Chavan, A.; Roy, N.

Pharmacophoric features of Pseudomonas aeruginosa deacetylase LpxC inhibitors: an electronic and structural analysis

Bioorg. Med. Chem. Lett.

17

861-868

2007

Pseudomonas aeruginosa

17188864

brenda

696705

Shin, H.; Gennadios, H.A.; Whittington, D.A.; Christianson, D.W.

Amphipathic benzoic acid derivatives: synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC

Bioorg. Med. Chem.

15

2617-2623

2007

Aquifex aeolicus (O67648)

17296300

brenda

697251

Kadam, R.U.; Garg, D.; Roy, N.

Selective mapping of chemical space for Pseudomonas aeruginosa deacetylase LpxC inhibitory potential

Chem. Biol. Drug Des.

71

45-56

2008

Pseudomonas aeruginosa

18086152

brenda

698451

Pirrung, M.C.; Tumey, L.N.; McClerren, A.L.; Raetz, C.R.

High-throughput catch-and-release synthesis of oxazoline hydroxamates. Structure-activity relationships in novel inhibitors of Escherichia coli LpxC: in vitro enzyme inhibition and antibacterial properties

J. Am. Chem. Soc.

125

1575-1586

2003

Escherichia coli

12568618

brenda

698550

Hyland, S.A.; Eveland, S.S.; Anderson, M.S.

Cloning, expression, and purification of UDP-3-O-acyl-GlcNAc deacetylase from Pseudomonas aeruginosa: a metalloamidase of the lipid A biosynthesis pathway

J. Bacteriol.

179

2029-2037

1997

Escherichia coli, Pseudomonas aeruginosa (P47205), Pseudomonas aeruginosa

9068651

brenda

698700

Young, K.; Silver, L.L.; Bramhill, D.; Cameron, P.; Eveland, S.S.; Raetz, C.R.; Hyland, S.A.; Anderson, M.S.

The envA permeability/cell division gene of Escherichia coli encodes the second enzyme of lipid A biosynthesis. UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase

J. Biol. Chem.

270

30384-30391

1995

Escherichia coli

8530464

brenda

698731

Hernick, M.; Gennadios, H.A.; Whittington, D.A.; Rusche, K.M.; Christianson, D.W.; Fierke, C.A.

UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase functions through a general acid-base catalyst pair mechanism

J. Biol. Chem.

280

16969-16978

2005

Escherichia coli, Aquifex aeolicus (O67848), Aquifex aeolicus

15705580

brenda

699038

Langsdorf, E.F.; Malikzay, A.; Lamarr, W.A.; Daubaras, D.; Kravec, C.; Zhang, R.; Hart, R.; Monsma, F.; Black, T.; Ozbal, C.C.; Miesel, L.; Lunn, C.A.

Screening for antibacterial inhibitors of the UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) using a high-throughput mass spectrometry assay

J. Biomol. Screen.

15

52-61

2009

Escherichia coli

20019290

brenda

699138

Kadam, R.U.; Garg, D.; Chavan, A.; Roy, N.

Evaluation of Pseudomonas aeruginosa deacetylase LpxC inhibitory activity of dual PDE4-TNFr inhibitors: a multiscreening approach

J. Chem. Inf. Model.

47

1188-1195

2007

Pseudomonas aeruginosa

17458951

brenda

699139

Kadam, R.U.; Shivange, A.V.; Roy, N.

Escherichia coli versus Pseudomonas aeruginosa deacetylase LpxC inhibitors selectivity: surface and cavity-depth-based analysis

J. Chem. Inf. Model.

47

1215-1224

2007

Escherichia coli, Pseudomonas aeruginosa (P47205), Pseudomonas aeruginosa

17441707

brenda

699420

Kline, T.; Andersen, N.H.; Harwood, E.A.; Bowman, J.; Malanda, A.; Endsley, S.; Erwin, A.L.; Doyle, M.; Fong, S.; Harris, A.L.; Mendelsohn, B.; Mdluli, K.; Raetz, C.R.; Stover, C.K.; Witte, P.R.; Yabannavar, A.; Zhu, S.

Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC

J. Med. Chem.

45

3112-3129

2002

Pseudomonas aeruginosa

12086497

brenda

699421

Pirrung, M.C.; Tumey, L.N.; Raetz, C.R.; Jackman, J.E.; Snehalatha, K.; McClerren, A.L.; Fierke, C.A.; Gantt, S.L.; Rusche, K.M.

Inhibition of the antibacterial target UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC): isoxazoline zinc amidase inhibitors bearing diverse metal binding groups

J. Med. Chem.

45

4359-4370

2002

Escherichia coli

12213077

brenda

699767

Robinet, J.J.; Gauld, J.W.

DFT investigation on the mechanism of the deacetylation reaction catalyzed by LpxC

J. Phys. Chem. B

112

3462-3469

2008

Aquifex aeolicus

18302359

brenda

700371

Coggins, B.E.; Li, X.; McClerren, A.L.; Hindsgaul, O.; Raetz, C.R.; Zhou, P.

Structure of the LpxC deacetylase with a bound substrate-analog inhibitor

Nat. Struct. Biol.

10

645-651

2003

Aquifex aeolicus

12833153

brenda

700924

Whittington, D.A.; Rusche, K.M.; Shin, H.; Fierke, C.A.; Christianson, D.W.

Crystal structure of LpxC, a zinc-dependent deacetylase essential for endotoxin biosynthesis

Proc. Natl. Acad. Sci. USA

100

8146-8150

2003

Aquifex aeolicus (O67648), Aquifex aeolicus

12819349

brenda

700934

Barb, A.W.; Jiang, L.; Raetz, C.R.; Zhou, P.

Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding

Proc. Natl. Acad. Sci. USA

104

18433-18438

2007

Escherichia coli, Aquifex aeolicus (O67648), Rhizobium leguminosarum (Q1ME43)

18025458

brenda

701103

Mochalkin, I.; Knafels, J.D.; Lightle, S.

Crystal structure of LpxC from Pseudomonas aeruginosa complexed with the potent BB-78485 inhibitor.

Protein Sci.

17

450-457

2008

Pseudomonas aeruginosa (P47205), Pseudomonas aeruginosa

18287278

brenda

718765

Ko, Y.; Chen, C.; Shieh, C.; Liu, Y.

Simultaneous purification and immobilization of D-hydantoinase on the immobilized metal affinity membrane via coordination bonds

Biochem. Eng. J.

61

20-27

2012

Escherichia coli

-

brenda

718865

Hernick, M.; Gattis, S.G.; Penner-Hahn, J.E.; Fierke, C.A.

Activation of Escherichia coli UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase by Fe2+ yields a more efficient enzyme with altered ligand affinity

Biochemistry

49

2246-2255

2010

Escherichia coli

20136146

brenda

719053

Mansoor, U.F.; Vitharana, D.; Reddy, P.A.; Daubaras, D.L.; McNicholas, P.; Orth, P.; Black, T.; Siddiqui, M.A.

Design and synthesis of potent Gram-negative specific LpxC inhibitors

Bioorg. Med. Chem. Lett.

21

1155-1161

2011

Escherichia coli

21273067

brenda

719894

Gattis, S.G.; Hernick, M.; Fierke, C.A.

Active site metal ion in UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) switches between Fe(II) and Zn(II) depending on cellular conditions

J. Biol. Chem.

285

33788-33796

2010

Escherichia coli

20709752

brenda

732992

Murphy-Benenato, K.; Olivier, N.; Choy, A.; Ross, P.; Miller, M.; Thresher, J.; Gao, N.; Hale, M.

Synthesis, structure, and SAR of tetrahydropyran-based LpxC inhibitors

ACS Med. Chem. Lett.

5

1213-1218A

2014

Escherichia coli, Pseudomonas aeruginosa, Aquifex aeolicus (O67648), Aquifex aeolicus, Escherichia coli W3110 / ATCC 27325

25408833

brenda

734239

Clayton, G.M.; Klein, D.J.; Rickert, K.W.; Patel, S.B.; Kornienko, M.; Zugay-Murphy, J.; Reid, J.C.; Tummala, S.; Sharma, S.; Singh, S.B.; Miesel, L.; Lumb, K.J.; Soisson, S.M.

Structure of the bacterial deacetylase LpxC bound to the nucleotide reaction product reveals mechanisms of oxyanion stabilization and proton transfer

J. Biol. Chem.

288

34073-34080

2013

Escherichia coli

24108127

brenda

734613

Tomaras, A.; McPherson, C.; Kuhn, M.; Carif, A.; Mullins, L.; George, D.; Desbonnet, C.; Eidem, T.; Montgomery, J.; Brown, M.; Reilly, U.; Miller, A.; O'Donnell, J.

LpxC Inhibitors as new antibacterial agents and tools for studying regulation of lipid a biosynthesis in Gram-negative pathogens

mBio

5

e01551-14

2014

Acinetobacter baumannii, Klebsiella pneumoniae, Pseudomonas aeruginosa

25271285

brenda

735205

Gao, N.; McLeod, S.; Hajec, L.; Olivier, N.; Lahiri, S.; Prince, D.; Thresher, J.; Ross, P.; Whiteaker, J.; Doig, P.; Li, A.; Hill, P.; Cornebise, M.; Reck, F.; Hale, M.

Overexpression of Pseudomonas aeruginosa LpxC with its inhibitors in an acrB-deficient Escherichia coli strain

Protein Expr. Purif.

104

57-64

2014

Pseudomonas aeruginosa (P47205), Pseudomonas aeruginosa

25240855

brenda

735297

Jana, S.; Loeppenberg, M.; Daniliuc, C.; Jose, J.; Holl, R.

Development of novel LpxC inhibitors: chiral-pool synthesis of C-triazolyl glycosides

Tetrahedron

69

9434-9442

2013

Escherichia coli

-

brenda

735298

Jana, S.; Loeppenberg, M.; Daniliuc, C.; Holl, R.

C-Triazolyl beta-D-furanosides as LpxC inhibitors: stereoselective synthesis and biological valuation

Tetrahedron

70

6569-6577

2014

Escherichia coli

-

brenda

735299

Jana, S.; Loeppenberg, M.; Daniliuc, C.; Holl, R.

Synthesis and biological evaluation of C-ethynyl furanosides as LpxC inhibitors

Tetrahedron

71

956-966

2015

Escherichia coli

-

brenda

752972

Kalinin, D.V.; Agoglitta, O.; Van de Vyver, H.; Melesina, J.; Wagner, S.; Riemann, B.; Schaefers, M.; Sippl, W.; Loeffler, B.; Holl, R.

Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC Synthesis, antibacterial properties, and docking studies

Bioorg. Med. Chem.

27

1997-2018

2019

Escherichia coli

30954331

brenda

753359

Kalinin, D.V.; Holl, R.

Insights into the zinc-dependent deacetylase LpxC biochemical properties and inhibitor design

Curr. Top. Med. Chem.

16

2379-2430

2016

Aquifex aeolicus (O67648), Escherichia coli (P0A727), Pseudomonas aeruginosa (P47205), Pseudomonas aeruginosa ATCC 15692 (P47205)

27072691

brenda

754390

Piizzi, G.; Parker, D.T.; Peng, Y.; Dobler, M.; Patnaik, A.; Wattanasin, S.; Liu, E.; Lenoir, F.; Nunez, J.; Kerrigan, J.; McKenney, D.; Osborne, C.; Yu, D.; Lanieri, L.; Bojkovic, J.; Dzink-Fox, J.; Lilly, M.D.; Sprague, E.R.; Lu, Y.; Wang, H.; Ranjitkar, S.; Xie, L.; Wang, B.; Glick, M.; Hamann, L.G.

Design, synthesis, and properties of a potent inhibitor of Pseudomonas aeruginosa deacetylase LpxC

J. Med. Chem.

60

5002-5014

2017

Pseudomonas aeruginosa

28549219

brenda

755346

Miller, M.; Gao, N.; Ross, P.; Olivier, N.

Crystal structure of A. aeolicus LpxC with bound product suggests alternate deacetylation mechanism

Proteins

83

1706-1719

2015

Aquifex aeolicus (O67648), Aquifex aeolicus

26177919

brenda

760065

Emiola, A.; Andrews, S.; Heller, C.; George, J.

Crosstalk between the lipopolysaccharide and phospholipid pathways during outer membrane biogenesis in Escherichia coli

Proc. Natl. Acad. Sci. USA

113

3108-3113

2016

Escherichia coli (P0A725), Escherichia coli, Escherichia coli K12 (P0A725)

26929331

brenda

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