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Ligand palmitoleoyl-[acyl-carrier protein]

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for palmitoleoyl-[acyl-carrier protein]

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.11

palmitoleoyl-[acyl-carrier protein] + reduced acceptor + O2 = (4Z,9Z)-hexadec-4,9-dienoyl-[acyl-carrier protein] + acceptor + H2O

734150

-

2.3.1.242

a palmitoleoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]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 = (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-((9Z)-hexadec-9-enoyloxy)tetradecanoyl]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 + an [acyl-carrier protein]

727828

-

2.3.1.242

a palmitoleoyl-[acyl-carrier protein] + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA = alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-(palmitoleoyl)-lipid IVA + a [acyl-carrier protein]

727617

-

2.3.1.242

2 entries

Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.46

hexadec-(9Z)-enoyl-[acyl-carrier protein] + reduced flavodoxin + O2 = ?

721562, 723623

-

1.14.14.46

palmitoleoyl-[acyl-carrier protein] + reduced flavodoxin + O2 = ?

718687

-

1.14.14.46

2 entries

1.14.19.11

palmitoleoyl-[acyl-carrier protein] + reduced acceptor + O2 = (4Z,9Z)-hexadec-4,9-dienoyl-[acyl-carrier protein] + acceptor + H2O

734150

-

2.3.1.179

palmitoleoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = cis-vaccenoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]

486916, 486919

-

2.3.1.242

a palmitoleoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]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 = (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-((9Z)-hexadec-9-enoyloxy)tetradecanoyl]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 + an [acyl-carrier protein]

728230, 727828

-

2.3.1.242

a palmitoleoyl-[acyl-carrier protein] + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA = alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-(palmitoleoyl)-lipid IVA + a [acyl-carrier protein]

727617

-

2.3.1.242

2 entries

2.3.1.41

cis-9-hexadecenoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = 3-oxo-cis-11-octadecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]

486863, 486917, 486916, 486919

-

3.1.2.14

palmitoleoyl-[acyl-carrier protein] + H2O = acyl-carrier protein + palmitoleic acid

716580

-

3.1.2.14

palmitoleoyl-[acyl-carrier protein] + H2O = palmitoleate + acyl-carrier protein

732664, 732615, 710244

-

3.1.2.14

palmitoleoyl-[acyl-carrier protein] + H2O = palmitoleic acid + acyl-carrier protein

649465, 731325

-

3.1.2.14

palmitoleoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + palmitoleate

751864, 666681

-

3.1.2.14

4 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.2

palmitoyl-[acyl-carrier protein] + AH2 + O2 = palmitoleoyl-[acyl-carrier protein] + A + H2O

-

-

6.2.1.20

ATP + palmitoleic acid + [acyl-carrier protein] = AMP + diphosphate + palmitoleoyl-[acyl-carrier protein]

-

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (16 results)

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Show Turnover Number (16 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.19.11

0.048

-

pH and temperature not specified in the publication

734150

3.1.2.14

0.0016

-

pH 8, 20°C, mutant M206W

732664

3.1.2.14

0.0062

-

pH 8, 20°C, mutant Q215W

732664

3.1.2.14

0.016

-

pH 8, 20°C, mutant T182W

732664

3.1.2.14

0.06

-

pH 8, 20°C

732615

3.1.2.14

0.1

-

pH 8, 20°C

732615

3.1.2.14

0.12

-

isozyme FatA, pH 8.0, 22°C

649465

3.1.2.14

0.15

-

pH 8.0, 22°C

716580

3.1.2.14

0.22

-

in 50 mM Tris-HCl buffer, pH 8.0, 5 mM DTT, at 22°C

710244

3.1.2.14

0.45

-

pH 8.0, 22°C

716580

3.1.2.14

0.6

-

pH 8, 20°C, mutant L118W

732664

3.1.2.14

0.74

-

isozyme FatB, pH 8.0, 22°C

649465

3.1.2.14

0.9

-

pH 8.0, 22°C, recombinant His-tagged enzyme

666681

3.1.2.14

1.62

-

in 50 mM Tris-HCl buffer, pH 8.0, 5 mM DTT, at 22°C

710244

3.1.2.14

6.08

-

isozyme FatB, pH 8.0, 22°C

649465

3.1.2.14

8

-

pH 8, 20°C, wild-type

732664

3.1.2.14

15 entries

K_M Value (20 results)

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Show KM Value (20 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.19.11

0.0021

-

pH and temperature not specified in the publication

734150

2.3.1.179

0.04

-

pH 7.2

486919

2.3.1.179

0.097

-

27°C

486916

2.3.1.179

0.216

-

37°C

486916

2.3.1.41

0.017

-

synthase II

486919

2.3.1.41

0.138

-

synthase I

486919

3.1.2.14

0.0001

-

pH 8, 20°C, mutant Q215W

732664

3.1.2.14

0.0002

-

pH 8, 20°C, mutant M206W

732664

3.1.2.14

0.0003

-

pH 8, 20°C, mutant L118W

732664

3.1.2.14

0.0003

-

pH 8, 20°C, wild-type

732664

3.1.2.14

0.00035

-

in 50 mM Tris-HCl buffer, pH 8.0, 5 mM DTT, at 22°C

710244

3.1.2.14

0.00035

-

pH 8.0, 22°C

716580

3.1.2.14

0.0005

-

pH 8, 20°C

732615

3.1.2.14

0.0006

-

pH 8.0, 22°C, recombinant His-tagged enzyme

666681

3.1.2.14

0.0006

-

pH 8, 20°C, mutant T182W

732664

3.1.2.14

0.00086

-

in 50 mM Tris-HCl buffer, pH 8.0, 5 mM DTT, at 22°C

710244

3.1.2.14

0.0022

-

pH 8, 20°C

732615

3.1.2.14

0.0026

-

isozyme FatB, pH 8.0, 22°C

649465

3.1.2.14

0.0049

-

isozyme FatA, pH 8.0, 22°C

649465

3.1.2.14

0.00551

-

pH 8.0, 22°C

716580

2.3.1.179

3 entries

2.3.1.41

2 entries

3.1.2.14

14 entries

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

486863

-

Acyl group transfer (acyl carrier protein)

1973

Vagelos, R.P.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

8

155-199

486916

7002930

Structural, enzymatic, and genetic studies of beta-ketoacyl-acyl carrier protein synthases I and II of Escherichia coli

1980

Garwin, J.L.; Klages, A.L.; Cronan, J.E.

J. Biol. Chem.

255

11949-11956

486917

5027749

Acyl carrier protein. XV. Studies of beta-ketoacyl-acyl carrier protein synthetase

1972

Alberts, A.W.; Bell, R.M.; Vagelos, P.R.

J. Biol. Chem.

247

3190-3198

486919

237914

Multiple forms of beta-ketoacyl-acyl carrier protein synthetase in Escherichia coli

1975

D'Agnolo, G.; Rosenfeld, I.S.; Vagelos, P.R.

J. Biol. Chem.

250

5289-5294

649465

12061798

Characterization of substrate specificity of plant FatA and FatB acyl-ACP thioesterases

2002

Salas, J.J.; Ohlrogge, J.B.

Arch. Biochem. Biophys.

403

25-34

666681

15841386

Cloning, characterization and structural model of a FatA-type thioesterase from sunflower seeds (Helianthus annuus L.)

2005

Serrano-Vega, M.J.; Garces, R.; Martinez-Force, E.

Planta

221

868-880

710244

20382402

Acyl-ACP thioesterases from castor (Ricinus communis L.): An enzymatic system appropriate for high rates of oil synthesis and accumulation

2010

Sanchez-Garcia, A.; Moreno-Perez, A.J.; Muro-Pastor, A.M.; Salas, J.J.; Garces, R.; Martinez-Force, E.

Phytochemistry

71

860-869

716580

21071236

Acyl-ACP thioesterases from macadamia (Macadamia tetraphylla) nuts: cloning, characterization and their impact on oil composition

2011

Moreno-Perez, A.J.; Sanchez-Garcia, A.; Salas, J.J.; Garces, R.; Martinez-Force, E.

Plant Physiol. Biochem.

49

82-87

718687

11368323

Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis

2000

Stok, J.E.; De Voss, J.

Arch. Biochem. Biophys.

384

351-360

721562

20658980

Selectivity in a barren landscape: the P450BioI-ACP complex

2010

Cryle, M.J.

Biochem. Soc. Trans.

38

934-939

723623

18838690

Structural insights from a P450 Carrier Protein complex reveal how specificity is achieved in the P450BioI ACP complex

2008

Cryle, M.J.; Schlichting, I.

Proc. Natl. Acad. Sci. USA

105

15696-15701

727617

20385763

Role of lipid A acylation in Yersinia enterocolitica virulence

2010

Pérez-Gutiérrez, C.; Llobet, E.; Llompart, C.M.; Reinés, M.; Bengoechea, J.A.

Infect. Immun.

78

2768-2781

727828

10092655

Effect of cold shock on lipid A biosynthesis in Escherichia coli. Induction At 12 degrees C of an acyltransferase specific for palmitoleoyl-acyl carrier protein

1999

Carty, S.M.; Sreekumar, K.R.; Raetz, C.R.

J. Biol. Chem.

274

9677-9685

728230

23434833

Identification of three genes encoding for the late acyltransferases of lipid A in Cronobacter sakazakii

2013

Cai, L.; Li, Y.; Tao, G.; Guo, W.; Zhang, C.; Wang, X.

Mar. Drugs

11

377-386

731325

24460945

Identification of novel acyl-ACP thioesterase gene ClFATB1 from Cinnamomum longepaniculatum

2013

Lin, N.; Ai, T.B.; Gao, J.H.; Fan, L.H.; Wang, S.H.; Chen, F.

Biochemistry

78

1298-1303

732615

25212866

Acyl-ACP thioesterases from Camelina sativa: Cloning, enzymatic characterization and implication in seed oil fatty acid composition

2014

Rodriguez-Rodriguez, M.F.; Salas, J.J.; Garces, R.; Martinez-Force, E.

Phytochemistry

107

7-15

732664

24327259

Effect of a mutagenized acyl-ACP thioesterase FATA allele from sunflower with improved activity in tobacco leaves and Arabidopsis seeds

2014

Moreno-Pérez, A.; Venegas-Calerón, M.; Vaistij, F.; Salas, J.; Larson, T.; Garcés, R.; Graham, I.; Martínez-Force, E.

Planta

239

669-677

734150

15939740

A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English ivy) can synthesize 16- and 18-carbon monoene and diene products

2005

Whittle, E.; Cahoon, E.; Subrahmanyam, S.; Shanklin, J.

J. Biol. Chem.

280

28169-28176

751864

29687516

The Lotus japonicus acyl-acyl carrier protein thioesterase FatM is required for mycorrhiza formation and lipid accumulation of Rhizophagus irregularis

2018

Brands, M.; Wewer, V.; Keymer, A.; Gutjahr, C.; Doermann, P.

Plant J.

95

219-232

Links to other databases for palmitoleoyl-[acyl-carrier protein]

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Show Links (1 entry)