Biosynthesis of the Aminocyclitol Subunit of Hygromycin A in Streptomyces hygroscopicus NRRL 2388

Chemistry and Biology

Volumn 16, Issue 11, 2009, Pages 1180-1189

  Palaniappan, Nadaraj ^a   Dhote, Vidya ^a   Ayers, Sloan ^a   Starosta, Agata L ^b   Wilson, Daniel N ^b   Reynolds, Kevin A ^a  

^a PORTLAND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

CHEMBIO; MICROBIO

Indexed keywords

ANTIINFECTIVE AGENT; CINNAMIC ACID DERIVATIVE; CYCLITOL; DRUG DERIVATIVE; HYGROMYCIN; HYGROMYCIN B;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; CYCLIZATION; DRUG EFFECT; ENZYMOLOGY; GENE DELETION; GENETICS; MULTIGENE FAMILY; MUTATION; OXIDATION REDUCTION REACTION; PROTEIN SYNTHESIS; STREPTOMYCES;

ANTI-BACTERIAL AGENTS; CINNAMATES; CYCLITOLS; CYCLIZATION; GENE DELETION; HYGROMYCIN B; MULTIGENE FAMILY; MUTATION; OXIDATION-REDUCTION; PROTEIN BIOSYNTHESIS; STREPTOMYCES;

ESCHERICHIA COLI; STREPTOMYCES HYGROSCOPICUS;

EID: 72049116264     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2009.10.013     Document Type: Article

References (40)

1. Ahlert J., Distler J., Mansouri K., and Piepersberg W. Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes. Arch. Microbiol. 168 (1997) 102-113
2. Bjorklund J.A., Frenzel T., Rueffer M., Kobayashi M., Mocek U., Fox C., Beale J.M., Grtiger S., Zenk M.H., and Floss H.G. Cryptic stereochemistry of berberine alkaloid biosynthesis. J. Am. Chem. Soc. 117 (1995) 1533-1545
3. Blum S., Groth I., Rohr J., and Fielder H.P. Biosynthetic capacities of actinomycetes. 5. Dioxolides, novel secondary metabolites from Streptomyces tendae. J. Basic Microbiol. 36 (1996) 19-25
4. Carter G.T., Goodman J.J., Torrey M.J., Borders D.B., and Gould S.J. Biosynthetic origin of the carbon skeleton of simaomicin alpha., a hexacyclic xanthone antibiotic. J. Org. Chem. 54 (1989) 4321-4323
5. Charan R.D., Schlingmann G., Bernan V.S., Feng X., and Carter G.T. Dioxapyrrolomycin biosynthesis in Streptomyces fumanus. J. Nat. Prod. 69 (2006) 29-33
6. Chida N., Nakazawa K., Ohtsuka M., Suzuki M., and Ogawa S. Total synthesis of methoxyhygromycin and its 5-epimer. Chem. Lett. 19 (1990) 423-426
7. Cui C.B., Han B., Caib B., and Wanga H. Pseudoverticin, a novel benzoquinone-derived ansamycin antibiotic obtained as new cell cycle inhibitor from Streptomyces pseudoverticillus YN17707. Tetrahedron Lett. 48 (2007) 4839-4843
8. Cundliffe E. How antibiotic-producing organisms avoid suicide. Annu. Rev. Microbiol. 43 (1989) 207-233
9. Dhote V., Gupta S., and Reynolds K.A. An O-phosphotransferase catalyzes phosphorylation of hygromycin A in the antibiotic-producing organism Streptomyces hygroscopicus. Antimicrob. Agents Chemother. 52 (2008) 3580-3588
10. Dinos G., Wilson D.N., Teraoka Y., Szaflarski W., Fucini P., Kalpaxis D., and Nierhaus K.H. Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding. Mol. Cell 13 (2004) 113-124
11. Flatt P.M., and Mahmud T. Biosynthesis of aminocyclitol-aminoglycoside antibiotics and related compounds. Nat. Prod. Rep. 24 (2007) 358-392
12. Guerrero M.D., and Modolell J. Hygromycin A, a novel inhibitor of ribosomal peptidyltransferase. Eur. J. Biochem. 107 (1980) 409-414
13. Gust B., Challis G.L., Fowler K., Kieser T., and Chater K.F. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. USA 100 (2003) 1541-1546
14. Habib e.-S.E., Scarsdale J.N., and Reynolds K.A. Biosynthetic origin of hygromycin A. Antimicrob. Agents Chemother. 47 (2003) 2065-2071
15. Hayashi S.F., Norcia L.J., Seibel S.B., and Silvia A.M. Structure-activity relationships of hygromycin A and its analogs: protein synthesis inhibition activity in a cell free system. J. Antibiot. (Tokyo) 50 (1997) 514-521
16. Hecker S.J., Lilley S.C., and Werner K.M. Hygromycin A: preparation of aminocyclitol analogs defining the minimum functionality required for biological activity. Bioorg. Med. Chem. Lett. 2 (1992) 1043-1046
17. Ikezawa N., Tanaka M., Nagayoshi M., Shinkyo R., Sakaki T., Inouye K., and Sato F. Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J. Biol. Chem. 278 (2003) 38557-38565
18. Kim S.D., Kweon M.H., Kim C.J., and Yoo I.D. Hygromycin, a plant growth inhibitor. Korean J. Biochem. 23 (1990) 23-25
19. Koda S., Morimoto Y., Yamashita M., Komori T., and Imanaka H. Studies on a new antibiotic FR-900109. 2. X-ray structure determination of FR-900109 p-bromophenyl ester. J. Antibiot. (Tokyo) 36 (1983) 1237-1238
20. Lai W.L., Chou L.Y., Ting C.Y., Kirby R., Tsai Y.C., Wang A.H., and Liaw S.H. The functional role of the binuclear metal center in D-aminoacylase: one-metal activation and second-metal attenuation. J. Biol. Chem. 279 (2004) 13962-13967
21. Lee H.B., Kim C.J., Kim J.S., Hong K.S., and Cho K.Y. A bleaching herbicidal activity of methoxyhygromycin (MHM) produced by an actinomycete strain Streptomyces sp. 8E-12. Lett. Appl. Microbiol. 36 (2003) 387-391
22. Mahmud T. The C7N aminocyclitol family of natural products. Nat. Prod. Rep. 20 (2003) 137-166
23. Mahmud T. Progress in aminocyclitol biosynthesis. Curr. Opin. Chem. Biol. 13 (2009) 161-170
24. Mahmud T., Flatt P.M., and Wu X. Biosynthesis of unusual aminocyclitol-containing natural products. J. Nat. Prod. 70 (2007) 1384-1391
25. Majumder A.L., Chatterjee A., Ghosh Dastidar K., and Majee M. Diversification and evolution of L-myo-inositol 1-phosphate synthase. FEBS Lett. 553 (2003) 3-10
26. Mann R.L., Gale R.M., and Van Abeele R.F. Hygromycin. II. Isolation and properties. Antibiot. Chemother. 3 (1953) 1279-1282
27. Nakagawa A., Fujimoto T., Omura S., Walsh J.C., Stotish R.L., and George B. Hygromycin A, an antitreponemal substance. II. Therapeutic effect for swine dysentery. J. Antibiot. (Tokyo) 40 (1987) 1627-1635
28. Omura S., Nakagawa A., Fujimoto T., Saito K., Otoguro K., and Walsh J.C. Hygromycin A, an antitreponemal substance. I. Screening method and therapeutic effect for Treponema hyodysenteriae-caused infection in CF-1 mice. J. Antibiot. (Tokyo) 40 (1987) 1619-1626
29. Palaniappan N., Ayers S., Gupta S., Habib e.-S., and Reynolds K.A. Production of hygromycin A analogs in Streptomyces hygroscopicus NRRL 2388 through identification and manipulation of the biosynthetic gene cluster. Chem. Biol. 13 (2006) 753-764
30. Pittenger R.C., Wolfe R.N., Hoehn P.N., Daily W.A., and McGuire J.M. Hygromycin. I. Preliminary studies in the production and biologic activity on a new antibiotic. Antibiot. Chemother. 3 (1953) 1268-1278
31. Pittner F., Tovarova I.I., Kornitskaya E.Y., Khokhlov A.S., and Hoffmann-Ostenhof O. Myo-inositol-1-phosphate synthase from Streptomyces griseus (studies on the biosynthesis of cyclitols, XXXVIII). Mol. Cell. Biochem. 25 (1979) 43-46
32. Sambrook J., and Russell D.W. Molecular Cloning: A Laboratory Manual. Third Edition (2001), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
33. Sipos L., and Szabo G. Myo-inositol-1-phosphate synthase in different Streptomyces griseus variants. FEMS Microbiol. Lett. 53 (1989) 339-343
34. Staley A.L., and Rinehart K.L. Biosynthesis of the streptovaricins: 3-amino-5-hydroxybenzoic acid as a precursor to the meta-C7N unit. J. Antibiot. (Tokyo) 44 (1991) 218-224
35. Szaflarski W., Vesper O., Teraoka Y., Plitta B., Wilson D.N., and Nierhaus K.H. New features of the ribosome and ribosomal inhibitors: non-enzymatic recycling, misreading and back-translocation. J. Mol. Biol. 380 (2008) 193-205
36. Uyeda M., Mizukami M., Yokomizo K., and Suzuki K. Pentalenolactone I and hygromycin A, immunosuppressants produced by Streptomyces filipinensis and Streptomyces hygroscopicus. Biosci. Biotechnol. Biochem. 65 (2001) 1252-1254
37. Wehmeier U.F., and Piepersberg W. Enzymology of aminoglycoside biosynthesis-deduction from gene clusters. Methods Enzymol. 459 (2009) 459-491
38. Yoshida M., Takahashi E., Uozumi T., and Beppu T. Hygromycin A and methoxyhygromycin A, novel inhibitors of K88 antigen synthesis of enterotoxic Escherichia coli strain. Agric. Biol. Chem. 50 (1986) 143-149
39. You-Young J., Kim S., Yang Y.Y., Kang C., Sohng J., and Suh J. Functional analysis of spectinomycin biosynthetic genes from Streptomyces spectabilis ATCC 27741. J. Microbiol. Biotechnol. 13 (2003) 906-911
40. Zhang X., and Parry R.J. Cloning and characterization of the pyrrolomycin biosynthetic gene clusters from Actinosporangium vitaminophilum ATCC 31673 and Streptomyces sp. strain UC 11065. Antimicrob. Agents Chemother. 51 (2007) 946-957