Mechanisms and structures of vitamin B 6-dependent enzymes involved in deoxy sugar biosynthesis

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1814, Issue 11, 2011, Pages 1534-1547

  Romo, Anthony J ^a,b   Liu, Hung Wen ^a,b  

^a The Center for Molecular Carcinogenesis and Toxicology   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Aminosugar; Biosynthesis; Deoxy sugar; Deoxygenation; Enzyme mechanism; Vitamin B 6 coenzyme

Indexed keywords

AMINOSUGAR; AMINOTRANSFERASE; DEOXYSUGAR; PYRIDOXINE;

CARBOHYDRATE SYNTHESIS; CATALYSIS; CRYSTAL STRUCTURE; DEOXYGENATION; ENZYME STRUCTURE; MUTATION; PRIORITY JOURNAL; REVIEW; TRANSAMINATION;

CATALYTIC DOMAIN; DEOXY SUGARS; GLYCINE; MODELS, MOLECULAR; PROTEIN CONFORMATION; TRANSAMINASES; VITAMIN B 6;

EID: 80054715742     PISSN: 15709639     EISSN: 18781454     Source Type: Journal    
DOI: 10.1016/j.bbapap.2011.02.003     Document Type: Review

References (109)

1. K. Brandenburg, A.B. Schromm, and T. Gutsmann Endotoxins: relationship between structure, function, and activity X. Wang, P.J. Quinn, Endotoxins: Structure, Function, and Recognition 2010 Springer Science+Business Media B.V. New York 53 67
2. A.C. Weymouth-Wilson The role of carbohydrates in biologically active natural products Nat. Prod. Rep. 14 1997 99 110 (Pubitemid 27191082)
3. D.A. Johnson, and H.-w. Liu Deoxysugars: occurrence, genetics, and mechanism of biosynthesis D. Barton, K. Nakanishi, O. Meth-Cohn, Comprehensive Chemistry of Natural Product Chemistry 1999 Pergamon New York 311 365
4. J.S. Thorson, T.J. Hosted, J.Q. Jiang, J.B. Biggins, and J. Ahlert Nature's carbohydrate chemists: the enzymatic glycosylation of bioactive bacterial metabolites Curr. Org. Chem. 5 2001 139 167 (Pubitemid 32421679)
5. V. Kren, and L. Martinkova Glycosides in medicine: the role of glycosidic residue in biological activity Curr. Med. Chem. 8 2001 1303 1328 (Pubitemid 32791798)
6. H.-w. Liu, and J.S. Thorson Pathways and mechanisms in the biosynthesis of novel deoxy sugars by bacteria Annu. Rev. Microbiol. 48 1994 223 256 (Pubitemid 24334097)
7. T.M. Hallis, and H.-w. Liu Learning nature's strategies for making deoxy sugars: pathways, mechanisms, and combinatorial applications Acc. Chem. Res. 32 1999 579 588
8. X. He, G. Agnihotri, and H.-w. Liu Novel enzymatic mechanisms in carbohydrate metabolism Chem. Rev. 100 2000 4615 4661 (Pubitemid 32090361)
9. X. He, and H.-w. Liu Formation of unusual sugars: mechanistic studies and biosynthetic applications Annu. Rev. Biochem. 71 2002 701 754 (Pubitemid 34800233)
10. C.J. Thibodeaux, C.E. Melancon III, and H.-w. Liu Unusual sugar biosynthesis and natural product glycodiversification Nature 446 2007 1008 1016 (Pubitemid 46676062)
11. C.J. Thibodeaux, C.E. Melancon III, and H.-w. Liu Natural-product sugar biosynthesis and enzymatic glycodiversification Angew. Chem. Int. Ed. 47 2008 9814 9859
12. C. Mendez, and J.A. Salas Altering the glycosylation pattern of bioactive compounds Trends Biotechnol. 19 2001 449 456 (Pubitemid 32972072)
13. S. Pelzer, A. Vente, and A. Bechthold Novel natural compounds obtained by genome-based screening and genetic engineering Curr. Opin. Drug Discov. Dev. 8 2005 228 238 (Pubitemid 40348974)
14. B.R. Griffith, J.M. Langenhan, and J.S. Thorson Sweetening natural products via glycorandomization Curr. Opin. Biotechnol. 16 2005 622 630 (Pubitemid 41654640)
15. C.J. Thibodeaux, and H.-w. Liu Manipulating nature's sugar biosynthetic machineries for glycodiversification of macrolides: recent advances and future prospects Pure Appl. Chem. 79 2007 785 799
16. C.J. Thibodeaux, H.-w. Liu, and J.S. Thorson Complimentary routes to natural product glycodiversification: pathway engineering and glycorandomization J.P. Kamerling, G.-J. Boons, Y. Lee, A. Suzuki, N. Taniguchi, A.G.J. Voragen, Comprehensive Glycoscience Vol. 3 2007 Elsevier Amsterdam 373 396
17. 6-dependent enzymes Curr. Opin. Struct. Biol. 8 1998 759 769 (Pubitemid 29004674)
18. K. Soda, T. Yoshimura, and N. Esaki Stereospecificity for the hydrogen transfer of pyridoxal enzyme reactions Chem. Rec. 1 2001 373 384 (Pubitemid 33771712)
19. A.C. Eliot, and J.F. Kirsch Pyridoxal phosphate enzymes: mechanistic, structural, and evolutionary considerations Annu. Rev. Biochem. 73 2004 383 415 (Pubitemid 39050374)
20. R. Percudani, and A. Peracchi A genomic overview of pyridoxal-dependent enzymes EMBO Rep. 4 2003 850 854
21. M.D. Toney Reaction specificity in pyridoxal phosphate enzymes Arch. Biochem. Biophys. 433 2005 279 287 (Pubitemid 39586598)
22. A. Nedal, and S.B. Zotchev Biosynthesis of deoxyaminosugars in antibiotic-producing bacteria Appl. Microbiol. Biotechnol. 64 2004 7 15 (Pubitemid 38392149)
23. M. Tanner Sugar nucleotide-modifying enzymes Curr. Org. Chem. 5 2001 169 192 (Pubitemid 32421680)
24. B.-Y. Hwang, B.-K. Chob, H. Yun, K. Koteshwar, and B.-G. Kim Revisit of aminotransferase in the genomic era and its application to biocatalysis J. Mol. Catal. B Enzym. 37 2005 47 55 (Pubitemid 41674647)
25. T.M. Weigel, V.P. Miller, and H.-w. Liu 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 1992 2140 2147
26. H. Chen, S.M. Yeung, N.L.S. Que, T. Müller, R.R. Schmidt, and H.-w. Liu Expression, purification, and characterization of TylB, an aminotransferase involved in the biosynthesis of mycaminose J. Am. Chem. Soc. 121 1999 7166 7167 (Pubitemid 29380557)
27. S.D. Breazeale, A.A. Ribeiro, and C.R. Raetz Origin of lipid A species modified with 4-amino-4-deoxy-l-arabinose in polymyxin-resistant mutants of Escherichia coli. An aminotransferase (ArnB) that generates UDP-4-deoxyl-l- arabinose J. Biol. Chem. 278 2003 24731 24739 (Pubitemid 37548630)
28. 6-dependent enzyme J. Am. Chem. Soc. 125 2003 5584 5585 (Pubitemid 36592853)
29. Z. Zhao, L. Hong, and H.-w. Liu Characterization of protein encoded by spnR from the spinosyn gene cluster of Saccharopolyspora spinosa: mechanistic implications for forosamine biosynthesis J. Am. Chem. Soc. 21 2005 7692 7693 (Pubitemid 40745954)
30. I.C. Schoenhofen, D.J. McNally, J.-R. Brisson, and S.M. Logan Elucidation of the CMP-pseudaminic acid pathway in Helicobacter pylori: synthesis from UDP-N-acetylglucosamine by a single enzymatic reaction Glycobiology 16 2006 8C 14C (Pubitemid 44390921)
31. I.C. Schoenhofen, V.V. Lunin, J.-P. Julien, Y. Li, E. Ajamian, A. Matte, M. Cygler, J.-R. Brisson, A. Aubry, S.M. Logan, S. Bhatia, W.W. Wakarchuk, and N.M. Young Structural and functional characterization of PseC, an aminotransferase involved in the biosynthesis of pseudaminic acid, an essential flagellar modification in Helicobacter pylori J. Biol. Chem. 281 2006 8907 8916 (Pubitemid 43847998)
32. L. Kaysser, L. Lutsch, S. Siebenberg, E. Wemakor, B. Kammerer, and B. Gust Identification and manipulation of the caprazamycin gene cluster lead to new simplified liponucleoside antibiotics and give insights into the biosynthetic pathway J. Biol. Chem. 284 2009 14987 14996
33. L.S. Engel The dilemma of multidrug-resistant gram-negative bacteria Am. J. Med. Sci. 340 2010 232 237
34. H. Zhang, J.A. White-Phillip, C.E. Melançon III, W.-l. Yu, H.-j. Kwon, and H.-w. Liu Elucidation of the kijanimicin gene cluster: insights into the biosynthesis of spirotetronate antibiotics and nitrosugars J. Am. Chem. Soc. 129 2007 14670 14683 (Pubitemid 350207880)
35. Y. Hu, A. Al-Mestarihi, C.L. Grimes, D. Kahne, and B.O. Bachmann A unifying nitrososynthase involved in nitrosugar biosynthesis J. Am. Chem. Soc. 130 2008 15756 15757
36. H.D. Johnson, and J.S. Thorson Characterization of CalE10, the N-oxidase involved in calicheamicin hydroxyaminosugar formation J. Am. Chem. Soc. 130 2008 17662 17663
37. N.A. Bruender, J.B. Thoden, and H.M. Holden X-ray structure of KijD3, a key enzyme involved in the biosynthesis of d-kijanose Biochemistry 49 2010 3517 3524
38. S. Timmons, and J.S. Thorson Increasing carbohydrate diversity via amine oxidation: aminosugar, hydroxyaminosugar, nitrososugar, and nitrosugar biosynthesis in bacteria Curr. Opin. Chem. Biol. 12 2008 297 305
39. K.K. Nepal, J.C. Yoo, and J.K. Sohng Biosynthetic approach for the production of new aminoglycoside derivative J. Biosci. Bioeng. 110 2010 109 112
40. A. Yonath Antibiotics targeting ribosomes: resistance, selectivity, synergism and cellular regulation Annu. Rev. Biochem. 74 2005 649 679 (Pubitemid 40995520)
41. J. Poehlsgaard, and S. Douthwaite The bacterial ribosome as a target for antibiotics Nat. Rev. Microbiol. 3 2005 870 881 (Pubitemid 41693182)
42. J.L. Hansen, J.A. Ippolito, N. Ban, P. Nissen, P.B. Moore, and T.A. Steitz The structures of four macrolide antibiotics bound to the large ribosomal subunit Mol. Cell 10 2002 117 128 (Pubitemid 34876566)
43. H.A. Kirst The spinosyn family of insecticides: realizing the potential of natural products research J. Antibiot. (Tokyo) 63 2010 101 111
44. S.A. Borisova, L. Zhao, D.H. Sherman, and H.-w. Liu Biosynthesis of desosamine: construction of a new macrolide carrying a genetically designed sugar moiety Org. Lett. 1 1999 133 136
45. M.W. Ruszczycky, S.H. Choi, and H.-w. Liu Stoichiometry of the redox neutral deamination and oxidative dehydrogenation reactions catalyzed by the radical SAM enzyme DesII J. Am. Chem. Soc. 132 2010 2359 2369
46. C.E. Melançon III, W.L. Yu, and H.-w. Liu TDP-mycaminose biosynthetic pathway revised and conversion of desosamine pathway to mycaminose pathway with one gene J. Am. Chem. Soc. 127 2005 12240 12241
47. C.E. Melançon III, L. Hong, J.A. White, H. Takahashi, Y.-n. Liu, and H.-w. Liu Characterization of TDP-4-keto-6-deoxy-d-glucose-3,4-isomerase (Tyl1a) from the TDP-d-mycaminose pathway of Streptomyces fradiae Biochemistry 46 2007 577 590 (Pubitemid 46105447)
48. C.E. Melançon III, and H.-w. Liu Engineered biosynthesis of macrolide antibiotics bearing the non-natural deoxysugars 4-epi-d-mycaminose and 3-N-monomethylamino-3-deoxy-d-fucose J. Am. Chem. Soc. 129 2007 4896 4897
49. L. Hong, Z. Zhao, C.E. Melançon III, H. Zhang, and H.-w. Liu In vivo characterization of the enzymes involved in TDP-d-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa J. Am. Chem. Soc. 130 2008 4954 4967 (Pubitemid 351500129)
50. P.D. Cook, and H.M. Holden GDP-perosamine synthase: structural analysis and production of a novel trideoxysugar Biochemistry 47 2008 2833 2840 (Pubitemid 351328834)
51. J.B. Thoden, C. Schffer, P. Messner, and H.M. Holden Structural analysis of QdtB, an aminotransferase required for the biosynthesis of dTDP-3-acetamido-3,6-dideoxy-α-d-glucose Biochemistry 48 2009 1553 1561
52. E.S. Burgie, and H.M. Holden Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine Biochemistry 46 2007 8999 9006 (Pubitemid 47237375)
53. E.S. Burgie, J.B. Thoden, and H.M. Holden Molecular architecture of DesV from Streptomyces venezuelae: a PLP-dependent transaminase involved in the biosynthesis of the unusual sugar desosamine Protein Sci. 16 2007 887 896 (Pubitemid 46683193)
54. I.C. Schoenhofen, D.J. McNally, E. Vinogradov, D. Whitfield, N.M. Young, S. Dick, W.W. Wakarchuk, J.-R. Brisson, and S.M. Logan Functional characterization of dehydratase/aminotransferase pairs from Helicobacter and Campylobacter: enzymes distinguishing the pseudaminic acid and bacillosamine biosynthetic pathways J. Biol. Chem. 281 2006 723 732
55. H.M. Holden, P.D. Cook, and J.B. Thoden Biosynthetic enzymes of unusual microbial sugars Curr. Opin. Struct. Biol. 2010 543 550
56. B.-Y. Hwang, H.-J. Lee, Y.-H. Yang, H.-S. Joo, and B.-G. Kim Characterization and investigation of substrate specificity of the sugar aminotransferase WecE from E. coli K12 Chem. Biol. 11 2004 915 925 (Pubitemid 38991786)
57. P.D. Cook, A.E. Carney, and H.M. Holden Accommodation of GDP-linked sugars in the active site of GDP-perosamine synthase Biochemistry 47 2008 10685 10693
58. L. Zhao, N.L.S. Que, Y. Xue, D.H. Sherman, and H.-w. Liu Biosynthesis of desosamine: probing the order of C-4 deoxygenation versus C-3 transamination J. Am. Chem. Soc. 120 1998 12159 12160 (Pubitemid 29012901)
59. X. He, and H.-w. Liu Mechanisms of enzymatic C - O bond cleavages in deoxyhexose biosynthesis Curr. Opin. Chem. Biol. 6 2002 590 597 (Pubitemid 35284189)
60. D.A. Johnson, and H.-w. Liu A mechanistic analysis of C - O bond cleavage events with a comparison to 3,6-dideoxysugar formation R. Cooper, J.D. Snyder, The Biology-Chemistry Interface: A Tribute to Koji Nakanishi 1999 Marcel Dekker New York 351 396
61. G. Samuel, and P. Reeves Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly Carbohydr. Res. 338 2003 2503 2519 (Pubitemid 37509950)
62. H. Chen, G. Agnihotri, Z. Guo, N.L.S. Que, X.H. Chen, and H.-w. Liu Biosynthesis of mycarose: isolation and characterization of enzymes involved in the C-2 deoxygenation J. Am. Chem. Soc. 121 1999 8124 8125 (Pubitemid 29430566)
63. L. Zhao, S.A. Borisova, S.-M. Yeung, and H.-w. Liu Study of C-4 deoxygenation in the biosynthesis of desosamine: evidence implicating a novel mechanism J. Am. Chem. Soc. 123 2001 7909 7910 (Pubitemid 32899357)
64. P.-h. Szu, X. He, L. Zhao, and H.-w. Liu Biosynthesis of TDP-d-desosamine: elucidation of a new strategy for C-4 deoxygenation Angew. Chem. Int. Ed. 44 2005
65. P.-h. Szu, M. Ruszczucky, S.H. Choi, F. Yan, and H.-w. Liu Characterization and mechanistic studies of DesII: a radical S-adenosyl-l-methionine enzyme involved in the biosynthesis of TDP-d-desosamine J. Am. Chem. Soc. 131 2009 14030 14042
66. 6 dependent novel bond cleavage reactions Pure Appl. Chem. 70 1998 9 16
67. 6 dependent enzyme catalysis Bioorg. Chem. 29 2001 234 257
68. P.M. Power, and M.P. Jennings The genetics of glycosylation in Gram-negative bacteria FEMS Microbiol. Lett. 218 2003 211 222 (Pubitemid 36183499)
69. T.M. Weigel, L.-d. Liu, and H.-w. Liu Mechanistic studies of the biosynthesis of 3,6-dideoxyhexoses in Yersinia pseudotuberculosis: purification and characterization of CDP-4-keto-6-deoxy-d-glucose-3-dehydrase Biochemistry 31 1992 2129 2139
70. P.A. Rubenstein, and J.L. Strominger Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses: VIII. Studies of the properties of E3 and its role in the formation of cytidine diphosphate-4-keto-3,6-dideoxyglucose J. Biol. Chem. 249 1974 3782 3788
71. J.S. Thorson, and H.-w. Liu 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 1993 7539 7540
72. 6 as a redox cofactor - a new role for an old coenzyme? J. Am. Chem. Soc. 115 1993 12177 12178 (Pubitemid 2004461)
73. Y. Lei, O. Ploux, and H.-w. Liu Mechanistic studies of CDP-6-deoxy-d-glycero-l-threo-4-hexulose-3-dehydrase: identification of His220 as the active-site base by chemical modification and site-directed mutagenesis Biochemistry 34 1995 4643 4654
74. G. Agnihotri, Y. Liu, B. Paschal, and H.-w. Liu Identification of an unusual [2Fe-2S]-binding motif in the dehydrase responsible for C-3 deoxygenation in the biosynthesis of 3,6-dideoxyhexoses Biochemistry 43 2004 14265 14274
75. P. Storici, D. De Biase, F. Bossa, S. Bruno, A. Mozzarelli, C. Peneff, R.B. Silverman, and T. Schirmer Structures of γ-aminobutyric acid (GABA) aminotransferase, a pyridoxal 5′-phosphate, and [2Fe-2S] cluster-containing enzyme, complexed with γ-ethynyl-GABA and with the antiepilepsy drug vigabatrin J. Biol. Chem. 279 2004 363 373 (Pubitemid 38044835)
76. P.A. Pieper, Z. Guo, and H.-w. Liu Mechanistic studies of 3,6-dideoxysugar biosynthesis: stereochemical course of C-3 deoxygenation J. Am. Chem. Soc. 117 1995 5158 5159
77. 3,4-glucoseen reductase based on its NADH:dichlorophenolindolphenol oxidoreductase activity J. Biol. Chem. 265 1990 8033 8041
78. 3,4- glucoseen reductase: exploration into a novel enzymatic C - O bond cleavage event Biochemistry 32 1993 11934 11942 (Pubitemid 23344721)
79. 3,4-glucoseen reductase from Yersinia pseudotuberculosis: enzyme purification and characterization of the cloned gene J. Bacteriol. 176 1994 460 468
80. 3,4-glucoseen reductase: the role of cysteine residues in catalysis as probed by chemical modification and site directed mutagenesis Biochemistry 34 1995 4159 4168
81. X. He, O. Ploux, and H.-w. Liu Biosynthesis of 3,6-dideoxyhexoses: in vivo and in vitro evidence for protein-protein interaction between CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase (E1) and its reductase (E3) Biochemistry 35 1996 16412 16420
82. 1) Biochemistry 35 1996 7879 7889 (Pubitemid 126552257)
83. D.A. Johnson, G.T. Gassner, V. Bandarian, F. Ruzicka, D.P. Ballou, G.H. Reed, and H.-w. Liu Kinetic characterization of an organic radical in the ascarylose biosynthetic pathway Biochemistry 35 1996 15846 15857
84. 6 radical in the ascarylose biosynthetic pathway J. Am. Chem. Soc. 122 2000 4239 4240 (Pubitemid 30304870)
85. P.A. Frey Lysine 2,3-aminomutase: is adenosylmethionine a poor man's adenosylcobalamine? FASEB J. 7 1993 662 670 (Pubitemid 23163601)
86. K.W. Lieder, S. Booker, F.J. Ruzicka, H. Beinert, G.H. Reed, and P.A. Frey S-adenosylmethionine-dependent reduction of lysine 2,3-aminomutase and observation of the catalytically functional iron-sulfur centers by electron paramagnetic resonance Biochemistry 37 1998 2578 2585 (Pubitemid 28119335)
87. B.W. Lepore, F.J. Ruzicka, P.A. Frey, and D. Ringe The X-ray crystal structure of lysine-2,3-aminomutase from Clostridium subterminale Proc. Natl Acad. Sci. USA 102 2005 13819 13824 (Pubitemid 41377662)
88. S.C. Wang, and P.A. Frey Binding energy in the one-electron reductive cleavage of S-adenosylmethionine in lysine 2,3-aminomutase, a radical SAM enzyme Biochemistry 46 2007 12889 12895 (Pubitemid 350086212)
89. 1 dehydrase: at the cross road of dehydration, aminotransferation and racemization Biochemistry 47 2008 6329 6341
90. 6-dependent enzyme Protein Sci. 15 2006 2093 2106 (Pubitemid 44316012)
91. P.D. Cook, and H.M. Holden A structural study of GDP-4-keto-6-deoxy-d- mannose-3-dehydratase: caught in the act of geminal diamine formation Biochemistry 46 2007 14215 14224 (Pubitemid 350250315)
92. P.D. Cook, and H.M. Holden GDP-4-keto-6-deoxy-d-mannose 3-dehydratase, accommodating a sugar substrate in the active site J. Biol. Chem. 283 2008 4295 4303
93. B. Popovic, X. Tang, D.Y. Chirgadze, F. Huang, T.L. Blundell, and J.B. Spencer Crystal structures of the PLP- and PMP-bound forms of BtrR, a dual functional aminotransferase involved in butirosin biosynthesis Proteins: Struct. Funct. Bioinf. 65 2006 220 230 (Pubitemid 44320630)
94. Q. Wu, Y.-n. Liu, H. Chen, E.J. Molitor, and H.-w. Liu A retro-evolution study of CDP-6-deoxy-d-glycero-l-threo-4-hexulose-3-dehydrase (E1): implications for C-3 deoxygenation in the biosynthesis of 3,6-dideoxyhexoses Biochemistry 46 2007 3759 3767 (Pubitemid 46493475)
95. J. Alam, N. Beyer, and H.-w. Liu Biosynthesis of colitose: expression, purification, and mechanistic characterization of GDP-4-keto-6-deoxy-d-mannose- 3-dehydrase (ColD) and GDP-l-colitose synthase (ColC) Biochemistry 43 2004 16450 16460 (Pubitemid 40041057)
96. H.J. Kim, J.A. White-Phillip, Y. Ogasawara, N. Shin, E.A. Isiorho, and H.-w. Liu The biosynthesis of spinosyn in Saccharopolyspora spinosa: synthesis of the methylated rhamnose and characterization of the functions of SpnH, SpnI, and SpnK J. Am. Chem. Soc. 132 2010 2901 2903
97. L. Hong, Z. Zhao, and H.-w. Liu Characterization of SpnQ from the spinosyn biosynthetic pathway of Saccharopolyspora spinosa: mechanistic and evolutionary implications for C-3 deoxygenation in deoxysugar biosynthesis J. Am. Chem. Soc. 128 2006 14262 14263 (Pubitemid 44707728)
98. H. Chen, Z. Guo, and H.-w. Liu The enzyme catalyzing the branched-chain coupling in the biosynthesis of yersiniose is a thiamine 5′-phosphate dependent flavoprotein J. Am. Chem. Soc. 120 1998 11796 11797
99. H. Chen, Z. Zhao, T.M. Hallis, Z. Guo, and H.-w. Liu Insights into the branched-chain formation of mycarose: methylation catalyzed by an S-adenosylmethionine-dependent methyltransferase Angew. Chem. Int. Ed. 40 2001 607 610 (Pubitemid 32144477)
100. H. Takahashi, Y.-n. Liu, H. Chen, and H.-w. Liu Biosynthesis of TDP-mycarose: the specificity of a single enzyme governs the outcome of the pathway J. Am. Chem. Soc. 127 2005 9340 9341 (Pubitemid 40934727)
101. H. Takahashi, Y.-n. Liu, and H.-w. Liu A two-stage one-pot enzymatic synthesis of TDP-l-mycarose from thymidine and glucose-1-phosphate J. Am. Chem. Soc. 128 2006 1432 1433 (Pubitemid 43214839)
102. N. Williams, and J. Wander Deoxy and branched-chain sugars W. Pigman, D. Horton, The Carbohydrates: Chemistry and Biochemistry Vol. 1B 1980 Academic Press New York 761 798
103. P. Lehwald, M. Richter, C. RÖhr, H.-w. Liu, and M. Müller Asymmetric intermolecular crossed aldehyde-ketone condensation through enzymatic carboligation reaction Angew. Chem. Int. Ed. 49 2010 2389 2392
104. L. Kaysser, L. Lutsch, S. Siebenberg, E. Wemakor, B. Kammerer, and B. Gust Identification and manipulation of the caprazamycin gene cluster lead to new simplified liponucleoside antibiotics and give insights into the biosynthetic pathway J. Biol. Chem. 284 2009 14987 14996
105. L. Kaysser, S. Siebenberg, B. Kammerer, and B. Gust Analysis of the liposidomycin gene cluster leads to the identification of new caprazamycin derivatives Chembiochem 11 2010 191 196
106. V. Schirch, and D.M.E. Szebenyi Serine hydroxymethyltransferase revisited Curr. Opin. Chem. Biol. 9 2005 482 487 (Pubitemid 41338200)
107. R. Florio, M. Luigi di Salvo, M. Vivoli, R. Contestabile, Serine hydroxymethyltransferase: a model enzyme for mechanistic, structural and evolutionary studies, Biochim. Biophys. Acta (in press), online.
108. S. Makart, M. Bechtold, and S. Panke Towards preparative asymmetric synthesis of β-hydroxy-α-amino acids: l-allo-threonine formation from glycine and acetaldehyde using recombinant GlyA J. Biotechnol. 130 2007 402 410 (Pubitemid 47021240)
109. S. Takayama, G.J. McGarvey, and C.-H. Wong Microbial aldolases and transketolases: new biocatalytic approaches to simple and complex sugars Annu. Rev. Microbiol. 51 1997 285 310 (Pubitemid 27433051)