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Chemical Compound Review:

TETRAHYD-CPD naphthalene-1,3,6,8-tetrol

Synonyms: SureCN704787, AG-E-34522, CHEBI:18365, CTK0H5975, AC1L98VM, ...

Feng, B. et al., Tsuji, G. et al., Ku, B. et al., Gross, F. et al., Fujii, I. et al., et al.

Fujii, Yasuoka, Tsai, Chang, Kwon-Chung, Ebizuka,

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Disease relevance of C04033

RppA, a chalcone synthase-related polyketide synthase (type III polyketide synthase) in the bacterium Streptomyces griseus, catalyzes the formation of 1,3,6,8-tetrahydroxynaphthalene (THN) from five molecules of malonyl-CoA [1].
Cultures of recombinant Pseudomonas sp. harbouring SoceCHS1 turned red upon incubation and the diffusible pigment formed was identified as 2,5,7-trihydroxy-1,4-naphthoquinone, the autooxidation product of 1,3,6,8-tetrahydroxynaphthalene [2].

High impact information on C04033

The pentaketide 1,3,6,8-tetrahydroxynaphthalene (T4HN) is a key precursor of 1,8-dihydroxynaphthalene-melanin, an important virulence factor in pathogenic fungi, where T4HN is believed to be the direct product of pentaketide synthases [3].
Flaviolin is a spontaneous oxidation product of 1,3,6,8-tetrahydroxynaphthalene (THN), which is biosynthesized in bacteria by a chalcone synthase-like (CS-like) type III polyketide synthase (PKS) [4].
We demonstrate construction and novel compound synthesis from a synthetic metabolic pathway consisting of a type III polyketide synthase (PKS) known as 1,3,6,8-tetrahydroxynaphthalene synthase (THNS) from Streptomyces coelicolor and soybean peroxidase (SBP) in a microfluidic platform [5].
We previously confirmed that the direct product of Pks1p is 1,3,6,8-tetrahydroxynaphthalene [6].
These results demonstrate that two enzymes, Thr1p and a deduced 1,3,6,8-tetrahydroxynaphthalene-specific reductase, are involved in the first reduction step of the melanin biosynthesis pathway of C. lagenarium [6].

Gene context of C04033

We report the inactivation, expression, and characterization of the type III PKS homologous SCO1206 gene product as 1,3,6,8-tetrahydroxynaphthalene synthase (THNS) [7].

Analytical, diagnostic and therapeutic context of C04033

To begin a genetic analysis of the initial synthetic steps leading to 1,8-DHN melanin biosynthesis, a 772-bp PCR product was amplified from genomic DNA using primers based on conserved regions of fungal polyketide synthases (Pks) known to produce the first cyclized 1,8-DHN-melanin pathway intermediate, 1,3,6,8-tetrahydroxynaphthalene [8].

References

Properties and substrate specificity of RppA, a chalcone synthase-related polyketide synthase in Streptomyces griseus. Funa, N., Ohnishi, Y., Ebizuka, Y., Horinouchi, S. J. Biol. Chem. (2002) [Pubmed]
Bacterial type III polyketide synthases: phylogenetic analysis and potential for the production of novel secondary metabolites by heterologous expression in pseudomonads. Gross, F., Luniak, N., Perlova, O., Gaitatzis, N., Jenke-Kodama, H., Gerth, K., Gottschalk, D., Dittmann, E., Müller, R. Arch. Microbiol. (2006) [Pubmed]
Hydrolytic polyketide shortening by ayg1p, a novel enzyme involved in fungal melanin biosynthesis. Fujii, I., Yasuoka, Y., Tsai, H.F., Chang, Y.C., Kwon-Chung, K.J., Ebizuka, Y. J. Biol. Chem. (2004) [Pubmed]
Identification and cloning of a type III polyketide synthase required for diffusible pigment biosynthesis in Saccharopolyspora erythraea. Cortés, J., Velasco, J., Foster, G., Blackaby, A.P., Rudd, B.A., Wilkinson, B. Mol. Microbiol. (2002) [Pubmed]
Chip-based polyketide biosynthesis and functionalization. Ku, B., Cha, J., Srinivasan, A., Kwon, S.J., Jeong, J.C., Sherman, D.H., Dordick, J.S. Biotechnol. Prog. (2006) [Pubmed]
Evidence for involvement of two naphthol reductases in the first reduction step of melanin biosynthesis pathway of Colletotrichum lagenarium. Tsuji, G., Sugahara, T., Fujii, I., Mori, Y., Ebizuka, Y., Shiraishi, T., Kubo, Y. Mycol. Res. (2003) [Pubmed]
Expression and characterization of the type III polyketide synthase 1,3,6,8-tetrahydroxynaphthalene synthase from Streptomyces coelicolor A3(2). Izumikawa, M., Shipley, P.R., Hopke, J.N., O'Hare, T., Xiang, L., Noel, J.P., Moore, B.S. J. Ind. Microbiol. Biotechnol. (2003) [Pubmed]
Molecular cloning and characterization of WdPKS1, a gene involved in dihydroxynaphthalene melanin biosynthesis and virulence in Wangiella (Exophiala) dermatitidis. Feng, B., Wang, X., Hauser, M., Kaufmann, S., Jentsch, S., Haase, G., Becker, J.M., Szaniszlo, P.J. Infect. Immun. (2001) [Pubmed]

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