Disease relevance of C03657

• The coenzyme A ester (2) is converted to 1,4-dihydroxy-2-naphthoic acid (3) by enzyme preparations from Mycobacterium phlei and Escherichia coli without any cofactor requirement [1].
• Conversion of o-succinylbenzoate to dihydroxynaphthoate by extracts of Micrococcus luteus [2].
• The missing enzyme in each group was identified by complementation of the cell-free extracts with o-succinylbenzoyl-coenzyme A (CoA) synthetase and dihydroxynaphthoate synthase extracted from Mycobacterium phlei [3].
• Identification of Bacillus subtilis men mutants which lack O-succinylbenzoyl-coenzyme A synthetase and dihydroxynaphthoate synthase [3].
• The deduced polypeptide sequence of open reading frame slr1736 reveals homology to chlorophyll synthase and 1,4-dihydroxy-2-naphthoic acid phytyltransferase in Synechocystis sp. strain PCC 6803 [4].

High impact information on C03657

• In the present work the presence of enzyme, 1,4-dihydroxy-2-naphthoate octaprenyltransferase, which catalyzes the conversion of 1,4-dihydroxy-2-naphthoate to demethylmenaquinone was demonstrated in cell extracts of E. coli [5].
• It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. coli [6].
• One of these, naphthoate synthase, forms the bicyclic ring system by catalyzing the conversion of o-succinylbenzoyl-coenzyme A to 1,4-dihydroxy-2-naphthoic acid [7].
• These men mutants fell into two groups: group I, in which the nutritional requirement was satisfied either by o-succinylbenzoic acid or by 1,4-dihydroxy-2-naphthoic acid; and group II, comprising those capable of growing only when supplemented with 1,4-dihydroxy-2-naphthoic acid [8].
• The enzymic conversion of the coenzyme A ester of 4-(2'-carboxyphenyl)-4-oxobutyric acid (i.e. o-succinylbenzoic acid) to 1,4-dihydroxy-2-naphthoic acid is a cyclization reaction which is part of menaquinone (vitamin K2) biosynthesis [9].

Chemical compound and disease context of C03657

• Aerobic culture of Propionibacterium freudenreichii ET-3 can increase production ratio of 1,4-dihydroxy-2-naphthoic acid to menaquinone [10].

Biological context of C03657

• Biosynthesis of menaquinones. Enzymatic prenylation of 1,4-dihydroxy-2-naphthoate by Micrococcus luteus membrane fractions [11].
• GDOxp formed a tetramer and exhibited high dioxygenase activity against 1,4-dihydroxy 2-naphthoate as well as gentisate, suggesting unusually broad substrate specificity [12].

Associations of C03657 with other chemical compounds

• These extracts converted o-succinylbenzoic acid (OSB) to 1,4-dihydroxy-2-naphthoic acid (DHNA) as shown by spectrophotofluorometric and radioactivity assays [2].

Gene context of C03657

• It was also shown that menA- and menB- strains accumulate 1,4-dihydroxy-2-naphthoic acid and 2-succinylbenzoic acid, respectively, in their culture supernatants [6].

References