Genes encoding enzymes responsible for biosynthesis of L-lyxose and attachment of eurekanate during avilamycin biosynthesis

Chemistry and Biology

Volumn 12, Issue 10, 2005, Pages 1137-1143

  Hofmann, Carsten ^a   Boll, Raija ^a   Heitmann, Björn ^b   Hauser, Gerd ^b   Dürr, Clemens ^a   Frerich, Anke ^a   Weitnauer, Gabriele ^a   Glaser, Steffen J ^b   Bechthold, Andreas ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AVILAMYCIN; CARBOXYLYASE; GLUCOSE; LYXOSE; OLIGOSACCHARIDE; PENTOSE; URIDINE DIPHOSPHATE GLUCURONATE DECARBOXYLASE;

ACTINOBACTERIA; ARTICLE; BIOSYNTHESIS; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; METABOLISM; MOLECULAR GENETICS;

ACTINOBACTERIA; CARBOHYDRATE SEQUENCE; CARBOXY-LYASES; ESCHERICHIA COLI; GLUCOSE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; PENTOSES;

ACTINOBACTERIA; ACTINOBACTERIA (CLASS); ESCHERICHIA COLI;

EID: 26944485142     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2005.08.016     Document Type: Article

References (38)

1. F. Buzzetti, F. Eisenberg, H.N. Grant, W. Keller-Schierlein, W. Voser, and H. Zähner Avilamycin Experientia 24 1968 320 324
2. G. Weitnauer, G. Hauser, C. Hofmann, U. Linder, R. Boll, K. Pelz, S.J. Glaser, and A. Bechthold Novel avilamycin derivatives with improved polarity generated by targeted gene disruption Chem. Biol. 11 2004 1403 1411
3. A.E. Belanger, and T.R. Shryock Avilamycin did not play a role in the discontinuation of evernimicin as a clinical drug candidate J. Mass. Spectrom. 40 2005 1109
4. L. Belova, T. Tenson, L. Xiong, P.M. McNicholas, and A.S. Mankin A novel site of antibiotic action in the ribosome: interaction of evernimicin with the large ribosomal subunit Proc. Natl. Acad. Sci. U. S. A. 98 2001 3726 3731
5. P.M. McNicholas, D.J. Najarian, P.A. Mann, D. Hesk, R.S. Hare, K.J. Shaw, and T.A. Black Evernimicin binds exclusively to the 50S ribosomal subunit and inhibits translation in cell-free systems derived from both Gram-positive and Gram-negative bacteria Antimicrob. Agents Chemother. 44 2000 1121 1126
6. P.M. McNicholas, P.A. Mann, D.J. Najarian, L. Miesel, R.S. Hare, and T.A. Black Effects of mutations in ribosomal protein L16 on susceptibility and accumulation of evernimicin Antimicrob. Agents Chemother. 45 2001 79 83
7. G. Weitnauer, A. Mühlenweg, A. Trefzer, D. Hoffmeister, R.D. Sussmuth, G. Jung, K. Welzel, A. Vente, U. Girreser, and A. Bechthold Biosynthesis of the orthosomycin antibiotic avilamycin A: deductions from the molecular analysis of the avi biosynthetic gene cluster of Streptomyces viridochromogenes Tü57 and production of new antibiotics Chem. Biol. 8 2001 569 581
8. I. Treede, G. Hauser, A. Mühlenweg, C. Hofmann, M. Schmidt, G. Weitnauer, S.J. Glaser, and A. Bechthold Genes involved in the formation and attachment of a two-carbon chain as component of methyleurekanate, a branched chain sugar moiety of avilamycin A Appl. Environ. Microbiol. 71 2005 400 406
9. P.A. Frey The Leloir pathway: a mechanistic imperative for three enzymes to change stereochemical configuration of a single carbon in galactose FASEB J. 10 1996 461 470
10. A.D. Hegeman, J.W. Gross, and P.A. Frey 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 2001 6598 6610
11. C. Gebb, D. Baron, and H. Grisebach Spectroscopic evidence for the formation of a 4-keto intermediate in the UDP-apiose/UDP-xylose synthase reaction Eur. J. Biochem. 54 1975 493 498
12. J.S. Schutzbach, and D.S. Feingold Biosynthesis of uridine diphosphate D-xylose. IV. Mechanism of action of uridine diphosphoglucuronate carboxy-lyase J. Biol. Chem. 245 1970 2476 2482
13. H. Jörnvall, B. Persson, M. Krook, S. Atrian, R. Gonzalez-Duarte, J. Jeffery, and D. Ghosh Short-chain dehydrogenases/reductases (SDR) Biochemistry 34 1995 6003 6013
14. H. Jörnvall Multiplicity and complexity of SDR and MDR enzymes Adv. Exp. Med. Biol. 463 1999 359 364
15. N. Tanaka, T. Nonaka, K. Nakamura, and A. Hara SDR structure, mechanism of action, and substrate recognition Curr. Org. Chem. 5 2001 89 111
16. K. Beis, S.T.M. Allard, A.D. Hegeman, G. Murshudov, D. Philp, and J.H. Naismith The structure of NADH in the enzyme dTDP-D-glucose dehydratase (RmlB) J. Am. Chem. Soc. 125 2003 11872 11878
17. P.Z. Gatzeva-Topalova, A.P. May, and M.C. Sousa Crystal structure of Escherichia coli ArnA (PmrI) decarboxylase domain. A key enzyme for lipid A modification with 4-amino-4-deoxy-L-arabinose and polymyxin resistance Biochemistry 43 2004 13370 13379
18. S.T.M. Allard, M.F. Giraud, C. Whitfield, M. Graninger, P. Messner, and J.H. Naismith The crystal structure of dTDP-D-glucose 4,6-dehydrogenase (RmlB) from Salmonella enterica serovar typhimurium, the second enzyme in the dTDP-L-rhamnose pathway J. Mol. Biol. 307 2001 283 295
19. M. Bar-Peled, C.L. Griffith, and T.L. Doering Functional cloning and characterization of a UDP-glucuronic acid decarboxylase: the pathogenic fungus Cryptococcus neoformans elucidates UDP-xylose synthesis Proc. Natl. Acad. Sci. USA 98 2001 12003 12008
20. M. Kobayashi, H. Nakagawa, I. Suda, I. Miyagawa, and T. Matoh Purification and cDNA cloning of UDP-D-glucuronate carboxy-lyase (UDP-D-xylose synthase) from pea seedings Plant Cell Physiol. 43 2002 1259 1265
21. T. Bililign, E.M. Shepard, J. Ahlert, and J.S. Thorson On the origin of deoxypentoses: evidence to support a glucose progenitor in the biosynthesis of calicheamicin Chembiochem 3 2002 1143 1146
22. F. Flett, V. Mersinias, and C.P. Smith High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl DNA-restricting streptomycetes FEMS Microbiol. Lett. 155 1997 223 229
23. D.J. MacNeil, K.M. Gewain, C.L. Ruby, G. Dezeny, P.H. Gibbons, and T. MacNeil Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector Gene 111 1992 61 68
24. S. Pelzer, W. Reichert, M. Huppert, D. Heckmann, and W. Wohlleben Cloning and analysis of a peptide synthetase gene of the balhimycin producer Amycolatopsis mediterranei DSM5908 and development of a gene disruption/replacement system J. Biotechnol. 56 1997 115 128
25. M. Biermann, R. Logan, K. O'Brien, E.T. Seno, R. Nagaraja, and B.E. Schoner Plasmid cloning vectors for conjugal transfer of DNA from Escherichia coli to Streptomyces spp Gene 166 1992 43 49
26. D. Hoffmeister, K. Ichinose, and A. Bechthold Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity Chem. Biol. 8 2001 557 567
27. J. Sambrook, E.F. Fritsch, and F. Maniatis Molecular Cloning: A Laboratory Manual Second Edition 1989 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
28. D.A. Hopwood, M.J. Bibb, K.F. Chater, T. Kieser, C.J. Bruton, H.M. Kieser, C.J. Bruton, H.M. Kieser, D.J. Lydiate, and C.P. Smith Genetic Manipulation of Streptomyces: A Laboratory Manual 1985 The John Innes Foundation Norwich, UK
29. S.F. Altschul, T.L. Madden, A.A. Schaffer, J. Zhang, Z. Zhang, W. Miller, and D.J. Lipmann Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res. 25 1997 3389 3402
30. 1H NMR spectra of proteins via double quantum filtering Biochem. Biophys. Res. Commun. 117 1983 479 485
31. L. Braunschweiler, and R.R. Ernst Coherence transfer by isotropic mixing: application to proton correlation spectroscopy J. Magn. Reson. 53 1983 521 528
32. A. Bax, and D.G. Davis Mlev-17-based two-dimensional homonuclear magnetization transfer spectroscopy J. Magn. Reson. 65 1985 355 360
33. S.J. Glaser, and J.J. Quant Homonuclear and heteronuclear Hartmann-Hahn transfer in isotropic liquids Adv. Magn. Opt. Reson. 19 1996 59 252
34. A.A. Bothner-By, R.L. Stephens, J.-M. Lee, C.D. Warren, and R.W. Jeanloz Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame J. Am. Chem. Soc. 106 1984 811 813
35. G. Bodenhausen, and D.J. Ruben Natural abundance N-15 NMR by enhanced heteronuclear spectroscopy Chem. Phys. Lett. 69 1980 185 189
36. M.F. Summers, L.G. Marzilli, and A. Bax Complete H-1 and C-13 assignments of coenzyme-B12 through the use of new two-dimensional NMR experiments J. Am. Chem. Soc. 108 1986 4285 4294
37. T.J. Norwood, J. Boyd, J.E. Heritage, N. Soffe, and I.D. Campbell Comparison of techniques for H-1-detected heteronuclear H-1-N-15 spectroscopy J. Magn. Reson. 87 1990 488 501
38. Goddard, T.D., and Kneller, D.G. (2001). Sparky 3 (computer program). University of California, San Francisco.