2002
DOI: 10.1021/ja0174682
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Definitive Evidence for Monoanionic Binding of 2,3-Dihydroxybiphenyl to 2,3-Dihydroxybiphenyl 1,2-Dioxygenase from UV Resonance Raman Spectroscopy, UV/Vis Absorption Spectroscopy, and Crystallography

Abstract: Ultraviolet resonance Raman spectroscopy (UVRRS), electronic absorption spectroscopy, and X-ray crystallography were used to probe the nature of the binding of 2,3-dihydroxybiphenyl (DHB) to the extradiol ring-cleavage enzyme, 2,3-dihydroxybiphenyl 1,2-dioxygenase (DHBD; EC 1.13.11.39). The lowest lying transitions in the electronic absorption spectrum of DHBD-bound DHB occurred at 299 nm, compared to 305 nm for the monoanionic DHB species in buffer. In contrast, the corresponding transitions in neutral and di… Show more

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Cited by 122 publications
(121 citation statements)
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“…When a substrate binds, these interactions are disrupted, as also noted for the analogous residues in BPHC_LB400 (79 O . This interaction is replaced by one with the acetate group of HPCA, which forms a hydrogen bond with both H248 ND1 and R293 O .…”
Section: Vol 186 2004 Structures Of Homoprotocatechuate 23-dioxygementioning
confidence: 70%
“…When a substrate binds, these interactions are disrupted, as also noted for the analogous residues in BPHC_LB400 (79 O . This interaction is replaced by one with the acetate group of HPCA, which forms a hydrogen bond with both H248 ND1 and R293 O .…”
Section: Vol 186 2004 Structures Of Homoprotocatechuate 23-dioxygementioning
confidence: 70%
“…By contrast, difference UVRR spectroscopy has been used to show that in extradiol dioxygenases, the asymmetry in the bound catechol is induced by mono-deprotonation of the Fe(II)-bound catechol. 28 Combining difference UVRR and optical spectroscopies is likely to provide other important insights into metal ligation in solution.…”
Section: Discussionmentioning
confidence: 99%
“…A conserved second sphere histidine (His241 in 2,3-dihydroxybiphenyl 1,2-dioxygenase) residue likely assists in substrate deprotonation. 28 The origin of the asymmetry in intradiol dioxygenases is unclear. Visible resonance Raman studies of catechol 1,2-dioxygenase (C12O) showed that the spectrum of the enzyme-substrate complex is similar to the spectra of model compounds containing Fe(III)-bound dianionic catechol, suggesting that the C12O-bound catechol is also dianionic.29 Dianionic binding is consistent with the increased Lewis acidity of the ferric center.…”
Section: Introductionmentioning
confidence: 99%
“…2,4,[6][7][8][9] This directly displaces two solvents from the "catalytic" face of the facial triad. The third solvent bond to the iron (if present) is weakened or broken by the donation of charge from the anionic catecholic ligand.…”
Section: Introductionmentioning
confidence: 99%