1,4-dihydroxy-2-naphthoyl-CoA hydrolase

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1,4-dihydroxy-2-naphthoyl-CoA hydrolase
Identifiers
EC no. 3.1.2.28
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The enzyme 1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28; systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase) catalyses the following reaction: [1] [2] [3]

1,4-dihydroxy-2-naphthoyl-CoA + H2O 1,4-dihydroxy-2-naphthoate + CoA

This enzyme participates in the biosynthesis of menaquinones, phylloquinone, and several plant pigments.

Related Research Articles

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

<span class="mw-page-title-main">Phytomenadione</span> Chemical compound

Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement. It is on the World Health Organization's List of Essential Medicines.

<span class="mw-page-title-main">Neocarzinostatin</span> Chemical compound

Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus.

In enzymology, juglone 3-monooxygenase (EC 1.14.99.27) is an enzyme that catalyzes the chemical reaction

In enzymology, a vitamin-K-epoxide reductase (warfarin-insensitive) is an enzyme that catalyzes the chemical reaction

In enzymology, a vitamin-K-epoxide reductase (warfarin-sensitive) is an enzyme that catalyzes the chemical reaction

In enzymology, an isochorismatase (EC 3.3.2.1) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Naphthoate synthase</span>

The enzyme 1,4-dihydroxy-2-naphthoyl-CoA synthase catalyzes the sixth step in the biosynthesis of phylloquinone and menaquinone, the two forms of vitamin K. In E. coli, 1,4-dihydroxy-2-naphthoyl-CoA synthase, formerly known as naphthoate synthase, is encoded by menB and uses O-succinylbenzoyl-CoA as a substrate and converts it to 1,4-dihydroxy-2-naphthoyl-CoA.

2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase, also known as SHCHC synthase is encoded by the menH gene in Escherichia coli and functions in the synthesis of vitamin K. The specific step in the synthetic pathway that SHCHC synthase catalyzes is the conversion of 5-enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate to (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate and pyruvate.

A hydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

A dihydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms (H) by hydroxyl groups (OH).

<span class="mw-page-title-main">Naphthazarin</span> Chemical compound

Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring organic compound with formula C
10
H
6
O
4
, formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.

<span class="mw-page-title-main">Naphthoquinone</span>

Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones:

2-Hydroxy-1,4-benzoxazin-3-one monooxygenase (EC 1.14.13.140, BX5 (gene), CYP71C3 (gene)) is an enzyme with systematic name 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one,NAD(P)H:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction

2,4-dihydroxy-1,4-benzoxazin-3-one-glucoside dioxygenase (EC 1.14.20.2, BX6 (gene), DIBOA-Glc dioxygenase) is an enzyme with systematic name (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside:oxygen oxidoreductase (7-hydroxylating). This enzyme catalyses the following chemical reaction

Demethylmenaquinone methyltransferase is an enzyme with systematic name S-adenosyl-L-methionine:demethylmenaquinone methyltransferase. This enzyme catalyses the following chemical reaction

2,4,7-trihydroxy-1,4-benzoxazin-3-one-glucoside 7-O-methyltransferase is an enzyme with systematic name S-adenosyl-L-methionine:(2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl β-D-glucopyranoside 7-O-methyltransferase. This enzyme catalyses the following chemical reaction

2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucosyltransferase is an enzyme with systematic name UDP-alpha-D-glucose:2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-beta-D-glucosyltransferase. This enzyme catalyses the following chemical reaction

1-4-dihydroxy-2-napthoate (DHNA) polyprenyltransferase (EC 2.5.1.74)is an enzyme that catalyzes the chemical reaction: all-trans-nonaprenyl diphosphate + 1-4-dihydroxy-2-napthoate + H+ demethylmenaquinol-9 + diphosphate + carbon dioxide

4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase (EC 3.2.1.182, DIMBOAGlc hydrolase, DIMBOA glucosidase) is an enzyme with systematic name (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside beta-D-glucosidase. This enzyme catalyses the following chemical reaction

References

  1. Widhalm, J.R.; van Oostende, C.; Furt, F.; Basset, G.J. (2009). "A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1". Proc. Natl. Acad. Sci. USA. 106 (14): 5599–5603. Bibcode:2009PNAS..106.5599W. doi: 10.1073/pnas.0900738106 . PMC   2660889 . PMID   19321747.
  2. Muller, W; Leistner, E (1976). "1,4-naphthoquinone, an intermediate in juglone (5-hydroxy-1,4-naphthoquinone) biosynthesis". Phytochemistry. 15 (3): 407–410. doi:10.1016/s0031-9422(00)86833-8.
  3. Eichinger D, Bacher A, Zenk MH, Eisenreich W (1999). "Quantitative assessment of metabolic flux by 13C NMR analysis. Biosynthesis of anthraquinones in Rubia tinctorum". J. Am. Chem. Soc. 121 (33): 7469–7475. doi:10.1021/ja990622o.