Abstract
The Kd values for the SO -23 -complex with 2, 7, 9-tricarboxy-PQQ were determined from pH 5.5 to 10.5. It was found that SO -23 and not HSO3 - is the nucleophile in this reaction. The midpoint potentials (Eo’) were also measured in this pH range for this quinone. A plot of Eo’ vs. pH produced a pKa = 8.44 for the dihydroquinone. As expected, a plot of Eo’ vs. the Kd for the PQQ-sulfite complex was linear. When NH +4 , was included, the sulfite adduct rapidly formed, however, a slow appearance of an unidentified species was evident. Eo’ for tricarboxy-PQQ + NH +4 were measured. pH titrations were carried out for oxidized tricarboxy-PQQ ± NH +4 and for the dihydroquinone form of this cofactor. The resulting pKa values are compared to corresponding literature values for PQQ analogs.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Duine, J.A., Frank, J., and Verwiel, P.E.J., 1981. Characterization of the second prosethetic group in methanol dehydrogenase from Hyphomicrobium X. Eur. J. Biochem. 118, 395–399.
Sleath, P.R., Noar, J.B., Eberlein, G.A., and Bruice, T.C., 1985. Synthesis of 7,9-didecarboxymethoxtin (4,5-Dihydro-4,5-dioxo-lH-pyrrolo-[2,3f]quinoline-2-carboxylic acid) and comparison of its chemical properties with those of methoxatin and analogous o-quinones. Model studies directed toward the action of PQQ requiring bacterial oxidore-ductases and plasma amine oxidase. J. Amer. Chem. Soc. 107, 3328–3338.
Eckert, T.S., Bruice, T.C., Gainor, J.A., and Weinreb, S.M., 1982. Some electrochemical and chemical properties of methoxatin and analogous quinones. Proc. Natl. Acad. Sci. USA 79, 2533–2536.
Muller, F. and Massey, V., 1969. Flavin-sulfite Complexes and their structure. J. Biol. Chem. 244, 4007–4016.
Rodriguez, E.J., Bruice, T.C., and Edmondson, D.E., 1987. Studies on the radical species of 9-decarboxymethoxatin. J. Amer. Chem. Soc. 109, 532–537.
Itoh, S., Ohshiro, Y., and Agawa, T., 1986. Reaction of reduced PQQ (PQQH2) and molecular oxygen. Bull. Chem. Soc. Japan 59, 1911–1914.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1989 Kluwer Academic Publishers
About this chapter
Cite this chapter
McIntire, W.S. (1989). Reaction of 2, 7, 9-Tricarboxy-PQQ with Nucleophiles. In: Jongejan, J.A., Duine, J.A. (eds) PQQ and Quinoproteins. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0957-1_34
Download citation
DOI: https://doi.org/10.1007/978-94-009-0957-1_34
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-6920-5
Online ISBN: 978-94-009-0957-1
eBook Packages: Springer Book Archive