Investigating the Role of the Geminal Dimethyl Groups of Coenzyme A: Synthesis and Studies of a Didemethyl Analogue

Bioorganic & Medicinal Chemistry - Tập 8 - Trang 2451-2460 - 2000
Kurt W Vogel1, Lucy M Stark2, Pranab K Mishra3, Wei Yang3, Dale G Drueckhammer3
1Department of Chemistry, Stanford University, Stanford, CA 94305 USA
2Department of Chemistry, Stanford University, Stanford, CA 94305, USA
3Department of Chemistry, State University at Stony Brook, Stony Brook, NY 11794, USA

Tài liệu tham khảo

Lee, C.-H.; Chen, A. F. In The Pyridine Nucleotide Coenzymes; Everse, J., Anderson, B., You, K., Eds.; Academic: New York, 1982; p 189. Primerano, D.; Burns, R. O. J. Bacteriol. 1982, 150, 1202. La Rossa, R. A.; VanDyk, T. K. J. Gen. Microbiol. 1989, 135, 2209. Fierke, C. A.; Jencks, W. P. J. Biol. Chem. 1986, 261, 7603. Whitty, A.; Fierke, C. A.; Jencks, W. P. Biochemistry 1995, 34, 11678. Lee, 1975, J. Am. Chem. Soc., 97, 1225, 10.1021/ja00838a043 Keire, 1992, J. Org. Chem., 57, 4427, 10.1021/jo00042a022 D'Ordine, 1995, Bioorg. Chem., 23, 169, 10.1006/bioo.1995.1014 Wu, 1998, J. Am. Chem. Soc., 120, 9988, 10.1021/ja982243l Barsukov, 1996, J. Mol. Biol., 262, 543, 10.1006/jmbi.1996.0534 Wu, 1997, Biochemistry, 36, 2211, 10.1021/bi962549+ For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521. Lin, 1999, Nature, 400, 86, 10.1038/21922 Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Wheeler, O. H.; de Rodriguez, E. E. G. J. Org. Chem. 1964, 29, 1227. Kirby, 1980, Adv. Phys. Org. Chem., 17, 183, 10.1016/S0065-3160(08)60129-X Airapetyan, G. M.; Zherebchenko, P. G.; Bystrova, V. M.; Benevolenskaya, Z. V.; Kuleshova, N. D.; Linkova, M. G.; Kildisheva, O. V.; Knunyants, I. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1967, 317. Howson, 1988, J. Med. Chem., 31, 352, 10.1021/jm00397a014 Knouzi, M.; Vaultier, M.; Carrie, R. Bull. Soc. Chim. Fr. 1985, 815. Oiry, 1986, J. Med. Chem., 29, 2217, 10.1021/jm00161a015 Dauben, 1995, Tetrahedron Lett., 44, 519 Shemin, D., Ed. Biochemical Preparations; John Wiley & Sons: New York, 1957; Vol. 5, p 1. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. Tetrahedron Lett. 1977, 155. O'Brien, 1976, Anal. Biochem., 76, 423, 10.1016/0003-2697(76)90337-7 Martin, 1993, Biochem. Biophys. Res. Commun., 192, 1155, 10.1006/bbrc.1993.1537 Martin, 1994, J. Am. Chem. Soc., 116, 4660, 10.1021/ja00090a014 Hirschbein, 1982, J. Org. Chem., 47, 3765, 10.1021/jo00140a036 Mohamadi, 1990, J. Comput. Chem., 11, 440, 10.1002/jcc.540110405 Pachler, 1964, Spectrochim. Acta, 20, 581, 10.1016/0371-1951(64)80055-2 Teller, J. H.; Powers, S. G.; Snell, E. E. J. Biol. Chem. 1976, 251, 3780. Aberhart, D. J. J. Am. Chem. Soc. 1979, 101, 1354. Epelbaum, 1998, J. Bacteriol., 180, 4056, 10.1128/JB.180.16.4056-4067.1998 Ketopantoate hydroxymethyltransferase, the enzyme that catalyzes the addition of the hydroxymethyl group to 11, has been shown to accept α-ketobutyrate but not pyruvate as a substrate; Powers, S. G.; Snell, E. E. J. Biol. Chem. 1976, 251, 3786. Miller, 1993, J. Mol. Evol., 36, 308 Bruice, T. C.; Pandit, K. P. J. Am. Chem. Soc. 1960, 82, 5858. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1997, 119, 9103. Bibart, 1999, J. Org. Chem., 64, 2903, 10.1021/jo981758s Mieyal, 1974, J. Biol. Chem., 249, 2633, 10.1016/S0021-9258(19)42777-4 Kunttu, 1989, Theochem, 184, 277, 10.1016/0166-1280(89)85097-3 Wu, 1998, J. Phys. Chem., 102, 9901, 10.1021/jp982164w Pauling, L. Festschr. Prof. Dr. Arthur Stoll Siebzigsten Geburstag 1958, 597. Fersht, 1980, Biochemistry, 19, 5520, 10.1021/bi00565a009 Izard, 1999, EMBO J., 18, 2021, 10.1093/emboj/18.8.2021