4-Hydroxybiphenyl

The degradation of 2-hydroxybiphenyl by Pseudomonas azelaica HBPl is initiated by 2-hydroxybiphenyl 3-monooxygenase (Suske et al. 1999). 

Suske WA, WJH van Berkel, H-P Kohler (1999) Catalytic mechanism of 2-hydroxybiphenyl 3-monooxygen-ase a flavoprotein from Pseudomonas azelaica HBPl. J Biol Chem 274 33355-33365. 

IGTS8 or simply IGTS8. The metabolic pathway in Rhodococcus sp. IGTS8 was delineated in the early 1990s [62], The pathway consists of four enzymes. DBT is converted to 2-hydroxybiphenyl (HBP) and sulfite via a 4-step pathway and the following intermediates DBT sulfoxide (dibenzothiophene-5-oxide, DBTO), DBT sulfone (dibenzothiophene-5,5-dioxide, DBT02) and hydroxyphenyl benzene sulfonate (phenol-phenyl sulfinate, HBPSi). 

A variation of the pathway in which 2 -hydroxybiphenyl-2-sulfinate is converted to 2 -hydroxybiphenyl-2-sulfonate (HBPSo) has been reported [26,62], In this alternate desulfurization pathway, the HBPSo further spontaneously cyclizes to sultone , BPSo. The latter is a substrate for DszA (Fig. 2), and is desulfurized to 2, 2 -dihydroxybiphenyl (DHBP) and sulfite. 

Wang, P., and Krawiec, S., Desulfurization of Dibenzothiophene to 2-Hydroxybiphenyl by Some Newly Isolated Bacterial Strains. Archives of Microbiology, 1994.161(3) pp. 266-271. 

Nakayama, N. Matsubara, T. Ohshiro, T., et al., A Novel Enzyme, 2 -Hydroxybiphenyl-2-Sulfinate Desulfinase (DszB), From a Dibenzothiophene-Desulfurizing Bacterium Rhodococcus Erythropolis KA2-5-1 Gene Overexpression and Enzyme Characterization. Biochimica Et Biophysica Acta-Proteins and Proteomics, 2002. 1598(1-2) pp. 122-130. 

The DszB enzyme encoded by the nucleotide sequence of ORF-2 catalyzes the conversion of HPBS to 2-hydroxybiphenyl and inorganic sulfur. 

The palladium-catalyzed arylation of 2-phenylphenols and naphthols shows an interesting feature of arylation of C-H bonds, leading to the formation of an (aryl)(aryloxy)palladium(n) intermediate.65,65a,65b The phenolates are suitable as precoordinating groups. The reaction of 2-hydroxybiphenyl with an excess of iodobenzene occurs regioselectively at the two ortho-positions of phenyl group under palladium catalysis (Equation (57)). In the case of 1-naphthol, the peri-position is phenylated (Equation (58)). 

An interesting example of the application of recombinant whole-cell biocatalysis is the conversion of 2-hydroxybiphenyl (2-phenylphenol) to 2,3-dihydroxybiphenyl... 

CASRN 90-43-7 molecular formula C12H10O FW 170.21 The rate constants for the reaction of OH radicals with 2-hydroxybiphenyl acid at 323 and 363 K were 18 x lO" and 10.50 x lO" cmVsec, respectively (Brubaker and Hites, 1998). 

Suske, W. A., M. Held, A. Schmidt, T. Fleischmann, M. G. Wubbolts, and H.-P. E. Kohler, Purification and characterization of 2-hydroxybiphenyl 3-monooxygenase, a novel NADH-dependent, FAD-containing aromatic hydroxylase from Pseudomonas azelaica HBP1 , J. Biol. Chem., 272, 24257-24265 (1997). 

Kohler, H-P. E., Kohler-Staub, D. Focht, D. D. (1988b). Degradation of 2-hydroxybiphenyl and 2,2 -dihydroxybiphenyl by Pseudomonassp. strain HBPl. Applied and Environmental Microbiology, 54, 2683-8. 

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