Mechanisms of enzymatic CO bond cleavages in deoxyhexose biosynthesis

Current Opinion in Chemical Biology - Tập 6 - Trang 590-597 - 2002
Xuemei He1, Hung-wen Liu1
1Division of Medicinal Chemistry, College of Pharmacy, Department of Chemistry and Biochemistry, University of Texas, Austin, Texas 78712, USA

Tài liệu tham khảo

Johnson, 1999, A mechanistic analysis of CO bond cleavage events with a comparison to 3,6-dideoxysugar formation, 351 Weymouth-Wilson, 1997, The role of carbohydrates in biologically active natural products, Nat Prod Rep, 14, 99, 10.1039/np9971400099 Johnson, 1999, Deoxsugars: occurrences, genetics, and mechanisms of biosynthesis, 3, 311 Hallis, 1999, Learning nature's strategies for making deoxy sugars: pathways, mechanisms, and combinatorial applications, Acc Chem Res, 32, 579, 10.1021/ar9602056 He, 2000, Novel enzymatic mechanisms in carbohydrate metabolism, Chem Rev, 100, 4615, 10.1021/cr9902998 He, 2002, Formation of unusual sugars: mechanistic studies and biosynthetic applications, Annu Rev Biochem, 71, 701, 10.1146/annurev.biochem.71.110601.135339 Frey, 1987, Complex pyridine nucleotide-dependent transformations, 461 Giraud, 2000, The rhamnose pathway, Curr Opin Struct Biol, 10, 687, 10.1016/S0959-440X(00)00145-7 Hutchinson, 1994, Drug synthesis by genetically engineered microorganisms, Biol Technol, 12, 375, 10.1038/nbt0494-375 Gross, 2000, Characterization of enzymatic processes by rapid mix-quench mass spectrometry: the case of dTDP-glucose 4,6-dehydratase, Biochemistry, 45, 13633, 10.1021/bi001963d Hallis, 1998, Stereospecificity of hydride transfer for the catalytically recycled NAD+ in CDP-d-glucose 4,6-dehydratase, Tetrahedron, 54, 15975, 10.1016/S0040-4020(98)01005-9 Wang, 1970, Biological mechanisms involved in the formation of deoxysugars. VI. Role and function of enzyme-bound nicotinamide adenine dinucleotide in thymidine diphosphate d-glucose oxidoreductase, J Biol Chem, 245, 8, 10.1016/S0021-9258(18)63415-5 Snipes, 1977, Stereochemistry of the dTDP-glucose oxidoreductase reaction, J Biol Chem, 252, 8113, 10.1016/S0021-9258(17)40946-X Russell, 1991, Stereochemical and mechanistic studies of CDP-d-glucose oxidoreductase isolated from Yersinia pseudotuberculosis, J Am Chem Soc, 113, 7777, 10.1021/ja00020a059 Yu, 1992, Mechanistic studies of the biosynthesis of 3,6-dideoxyhexoses in Yersinia pseudotuberculosis. Purification and stereochemical analysis of CDP-d-glucose oxidoreductase, J Biol Chem, 267, 5868, 10.1016/S0021-9258(18)42634-8 Bauer, 1992, The molecular structure of UDP-galactose 4-epimerase from Escherichia coli determined at 2.5 Å resolution, Prot Struct Funct Genet, 12, 372, 10.1002/prot.340120409 Hegeman, 2001, Probing catalysis by Escherichia coli dTDP-glucose-4,6-dehydratase: identification and preliminary characterization of functional amino acid residues at the active site, Biochemistry, 40, 6598, 10.1021/bi010441a Gerratana, 2001, Mechanistic roles of Thr134, Tyr160, and Lys164 in the reaction catalyzed by dTDP-glucose 4,6-dehydratase, Biochemistry, 40, 9187, 10.1021/bi0108249 Gross, 2001, Dehydration is catalyzed by glutamate-136 and aspartic acid-135 active site residues in Escherichia coli dTDP-glucose 4,6-dehydratase, Biochemistry, 40, 12497, 10.1021/bi011138c Chang, 1998, CDP-6-deoxy-6,6-difluoro-d-glucose: a mechanism-based inhibitor for CDP-D-glucose 4,6-dehydratase, J Am Chem Soc, 120, 9698, 10.1021/ja982198h Hegeman, 2002, Concerted and stepwise dehydration mechanisms observed in wild-type and mutated Escherichia coli dTDP-glucose 4,6-dehydratase, Biochemistry, 41, 2797, 10.1021/bi011748c Stubbe, 1998, Protein radicals in enzyme catalysis, Chem Rev, 98, 705, 10.1021/cr9400875 Draeger, 1999, Mechanism of the 2-deoxygenation step in the biosynthesis of the deoxyhexose moieties of the antibiotics granaticin and oleandomycin, J Am Chem Soc, 121, 2611, 10.1021/ja9837250 Chen, 1999, Biosynthesis of mycarose: isolation and characterization of enzymes involved in the C-2 deoxygenation, J Am Chem Soc, 121, 8124, 10.1021/ja991713o Thorson, 1993, Characterization of the first PMP-dependent iron–sulfur-containing enzyme which is essential for the biosynthesis of 3,6-dideoxyhexoses, J Am Chem Soc, 115, 7539, 10.1021/ja00069a078 Lei, 1995, Mechanistic studies on CDP-6-deoxy-l-threo-d-glycero-4-hexulose 3-dehydrase: identification of His-220 as the active-site base by chemical modification and site-directed mutagenesis, Biochemistry, 34, 4643, 10.1021/bi00014a018 Weigel, 1992, Mechanistic and stereochemical studies of a unique dehydration catalyzed by CDP-4-keto-6-deoxy-d-glucose-3-dehydrase: a pyridoxamine 5′-phosphate dependent enzyme isolated from Yersinia pseudotuberculosis, Biochemistry, 31, 2140, 10.1021/bi00122a035 Miller, 1993, Cofactor characterization and mechanistic studies of CDP-6-deoxy-Δ3,4-glucoseen reductase: exploration into a novel enzymatic CO bond cleavage event, Biochemistry, 32, 11934, 10.1021/bi00095a025 Gassner, 1996, Kinetics of the reductive half-reaction of the iron-sulfur flavoenzyme CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase reductase, Biochemistry, 35, 7752, 10.1021/bi960217z Johnson, 1996, Kinetic characterization of an organic radical in the ascarylose biosynthetic pathway, Biochemistry, 35, 15846, 10.1021/bi961370w Chang, 2000, Characterization of a unique coenzyme B6 radical in the ascarylose biosynthetic pathway, J Am Chem Soc, 122, 4239, 10.1021/ja0000807 Xue, 1998, A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity, Proc Natl Acad Sci USA, 95, 12111, 10.1073/pnas.95.21.12111 Zhao, 1998, Biosynthesis of desosamine: molecular evidence suggesting β-glucosylation as a self-resistance mechanism in methymycin/neomethymycin producing strain, Streptomyces venezuelae, J Am Chem Soc, 120, 9374, 10.1021/ja981500j Zhao, 2001, Study of C-4 deoxygenation in the biosynthesis of desosamine: evidence implicating a novel mechanism, J Am Chem Soc, 123, 7909, 10.1021/ja010587x Ruzicka, 2000, Lysine 2,3-aminomutase from Clostridium subterminale SB4: mass spectral characterization of cyanogen bromide-treated peptides and cloning, sequencing, and expression of the gene kamA in Escherichia coli, J Bacteriol, 182, 469, 10.1128/JB.182.2.469-476.2000 Frey, 1999, Radical reactions featuring lysine 2,3-aminomutase, 5, 205 Frey, 2000, Radical mechanisms in adenosylmethionine- and adenosylcobalamin-dependent enzymatic reactions, Arch Biochem Biophys, 382, 6, 10.1006/abbi.2000.2010 Frey, 2001, Radical mechanisms of enzymatic catalysis, Annu Rev Biochem, 70, 121, 10.1146/annurev.biochem.70.1.121 Sofia, 2001, Radical SAM, a novel protein superfamily linking unresolved steps in familiar biosynthetic pathways with radical mechanisms: functional characterization using new analysis and information visualization methods, Nucleic Acid Res., 29, 1097, 10.1093/nar/29.5.1097 LoBrutto, 2001, 5′-Deoxyadenosine contacts the substrate radical intermediate in the active site of ethanolamine ammonia-lyase: 2H and 13C electron nuclear double resonance studies, Biochemistry, 40, 9, 10.1021/bi001865s