Significance of the 20-kDa subunit of heterodimeric 2-deoxy-scyllo-inosose synthase for the biosynthesis of butirosin antibiotics in bacillus circulans

Bioscience, Biotechnology and Biochemistry

Volumn 66, Issue 7, 2002, Pages 1538-1545

  Tamegai, Hideyuki ^a   Nango, Eriko ^a   Koike Takeshita, Ayumi ^a   Kudo, Fumitaka ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

2 deoxy scyllo inosose synthase; 20 kDa subunit; Butirosin binsynthesis

Indexed keywords

2 DEOXY SCYLLO INOSOSE SYNTHASE; 2-DEOXY-SCYLLO-INOSOSE SYNTHASE; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; BUTIROSIN; LYASE;

AMINO ACID SEQUENCE; ARTICLE; BACILLUS; BACTERIAL GENE; BIOSYNTHESIS; ESCHERICHIA COLI; GENETICS; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; MICROBIOLOGICAL EXAMINATION; MOLECULAR CLONING; MOLECULAR GENETICS; POLYACRYLAMIDE GEL ELECTROPHORESIS; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; BACILLUS; BACTERIAL PROTEINS; BUTIROSIN SULFATE; CLONING, MOLECULAR; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ESCHERICHIA COLI; GENES, BACTERIAL; KINETICS; LYASES; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

BACILLUS CIRCULANS; BACILLUS SUBTILIS; ESCHERICHIA COLI;

EID: 0036653432     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.66.1538     Document Type: Article

References (37)

1. Cho, J. and Rando, R. R., Specificity in the binding of aminoglycosides to HIV-RRE RNA. Biochemistry, 38, 8548-8554 (1999).
2. Litovchick, A., Evdokimov, A. G., and Lapidot, A., Aminoglycoside-arginine conjugates that bind TAR RNA: synthesis, characterization, and antiviral activity. Biochemistry, 39, 2838-2852 (2000).
3. Distler, J., Mansouri, K., Mayer, G., Stockmann, M., and Piepersberg, W., Streptomycin biosynthesis and its regulation in Streptomycetes. Gene, 115, 105-111 (1992).
4. Dairi, T., Ohta, T., Hashimoto, E., and Hasegawa, M., Self cloning in Micromonospora olivasterospora of fms genes for fortimicin A (astromicin) biosynthesis. Mol. Gen. Genet., 232, 262-270 (1992).
5. Ahlert, J., Distler, J., Mansouri, K., and Pieper sberg, W., Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing streptomycetes. Arch. Microbiol., 168, 102-113 (1997).
6. Rosi, D., Goss, W. A., and Daum, S. J., Mutational biosynthesis by idiotrophs of Micromonospora purpurea I. Conversion of aminocyclitols to new aminoglycoside antibiotics. J. Antibiotics, 30, 88-97 (1977).
7. Daum, S. J., Rosi, D., and Goss, W. A., Mutational biosynthesis by idiotrophs of Micromonospora purpurea II. Conversion of non-amino containing cyclitols to aminoglycoside antibiotics. J. Antibiotics, 30, 98-105 (1977).
8. Furumai, T., Takeda, K., Kinumaki, A., Ito, Y., and Okuda, T., Biosynthesis of Butirosins. II Biosynthetic pathway of butirosins elucidated from cosynthesis and feeding experiments. J. Antibiotics, 32, 891-899 (1979).
9. Fujiwara, T., Takahashi, Y., Matsumoto, K., and Kondo, E., Isolation of an intermediate of 2-deoxys-treptamine biosynthesis from a mutant of Bacillus cir-culans. J. Antibiotics, 33, 824-829 (1980).
10. Kase, H., Iida, T., Odakura, Y., Shirahata, K., and Nakayama, K., Accumulation of 2-deoxy-inosamine by a 2-deoxystreptamine-requiring idiotroph of Micromonospora sagamiensis. J. Antibiotics, 33, 1210-1212 (1980).
11. Aubert-Pivert, E. and Davies, J., Biosynthesis of butirosin in Bacillus circulans NRRL B3312: identification by sequence analysis and insertional mutagenesis of the butB gene involved in antibiotic production. Gene, 147, 1-11 (1994).
12. Suzukake, K., Tokunaga, K., Hayashi, H., Hori, M., Uehara, Y., Ikeda, D., and Umezawa, H., Biosynthesis of 2-deoxystreptamine. J. Antibiotics, 38, 1211-1218 (1985).
13. Lucher, L. A., Chen, Y.-M., and Walker, J. B., Reactions catalyzed by purified L-glutamine:keto-scyllo-inositol aminotransferase, an enzyme required for biosynthesis of aminocyclitol antibiotics. An-timicrob. Agents Chemother., 33, 452-459 (1989).
14. Yamauchi, N. and Kakinuma, K., Confirmation of in vitro synthesis of 2-deoxy-scyllo-inosose, the earliest intermediate in the biosynthesis of 2-deoxystrepta-mine, using cell free preparations of Streptomyces fradiae. J. Antibiotics, 45, 774-780 (1992).
15. Yamauchi, N. and Kakinuma, K., Enzymatic carbocycle formation in microbial secondary metabolism. The mechanism of the 2-deoxy-scyllo-inosone synthase reaction as a crucial step in the 2-deoxystreptamine biosynthesis in Streptomyces fra-diae. J. Org. Chem., 60, 5614-5619 (1995).
16. Kudo, F., Yamauchi, N., Suzuki, R., and Kakinuma, K., Kinetic isotope effect and reaction mechanism of 2-deoxy-scyllo-inosose synthase derived from butirosin-producing Bacillus circulans. J. Antibiotics, 50, 424-428 (1997).
17. Iwase, N., Kudo, F., Yamauchi, N., and Kakinuma, K., Substrate specificity of 2-deoxy-scyllo-inosose synthase, the starter enzyme for 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates and proposed mechanism. Biosci. Biotechnol. Biochem., 62, 2396-2407 (1998).
18. 2H NMR spectroscopy. J. Am. Chem. Soc., 103, 5614-5616 (1981).
19. Kakinuma, K., Ogawa, Y., Sasaki, T., Seto, H., and Otake, N., Mechanism and stereochemistry of the biosynthesis of 2-deoxystreptamine and neosamine C. J. Antibiotics, 42, 926-933 (1989).
20. Kudo, F., Hosomi, Y., Tamegai, H., and Kakinuma, K., Purification and characterization of 2-deoxy-scyl-lo-inosose synthase derived from Bacillus circulans. A crucial carbocyclization enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics. J. Antibiotics, 52, 81-88 (1999).
21. Kudo, F., Tamegai, H., Fujiwara, T., Tagami, U., Hirayama, K., and Kakinuma, K., Molecular cloning of the gene for the key carbocycle-forming enzyme in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics and its comparison with de-hydroquinate synthase. J. Antibiotics, 52, 559-571 (1999).
22. Ota, Y., Tamegai, H., Kudo, F., Kuriki, H., Koike-Takeshita, A., Eguchi, T., and Kakinuma, K., Butirosin-biosynthetic gene cluster from Bacillus cir-culans. J. Antibiotics, 53, 1158-1167 (2000).
23. Yoshida, K., Ishio, I., Nagakawa, E., Yamamoto, Y., Yamamoto, M., and Fujita, Y., Systematic study of gene expression and transcription organization in the gntZ-ywaA region of the Bacillus subtilis genome. Microbiology, 146, 573-579 (2000).
24. Schagger, H. and von Jagow, G., Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal. Biochem., 166, 368-379 (1987).
25. Sambrook, J., Fritsch, E. F., and Maniatis, T., Molecular cloning: A laboratory manual. 2nd ed. Cold Spring Harbor Laboratory, New York (1989).
26. Itaya, M., Construction of a novel tetracycline resistance gene cassette useful as a marker on the Bacillus subtilis chromosome. Biosci. Biotechnol. Biochem., 56, 685-686 (1992).
27. Fujiwara, T. and Kondo, E., Biosynthetic pathway of 2-deoxystreptamine. J. Antibiotics, 34, 13-15 (1981).
28. Davis, B. J., Disk electrophoresis-II method and application to human serum proteins. Ann. N. Y. Acad. Sci., 121, 404-427 (1964).
29. Laemmli, U. K., Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680-685 (1970).
30. Ogasawara, N., Nakai, S., and Yoshikawa, H., Systematic sequencing of the 180 kilobase region of the Bacillus subtilis chromosome containing the replication origin. DNA Res., 1, 1-14 (1994).
31. Takami, H., Takaki, Y., Nakasone, Y., Sakiyama, T., Maeno, G., Sasaki, R., Hirama, C., Fuji, F., and Masui, N., Genetic analysis of the chromosome of alkaliphilic Bacillus halodurans C-125. Extremo-philes, 3, 227-233 (1999).
32. Henner, D. J., Band, L., Flaggs, G., and Chen, E., The organization and nucleotide sequence of the Bacillus subtilis hisH, tyrA and aroE genes. Gene, 49, 147-152 (1986).
33. Klem, T. J. and Davisson, V. J., Imidazole glycerol phosphate synthase: the glutamine amidotransferase in histidine biosynthesis. Biochemistry, 32, 5177-5186 (1993).
34. 6 biosynthesis. Proc. Natl. Acad. Sci. USA, 96, 9374-9378 (1999).
35. Tanaka, K., Tazuya, K., Yamada, K., and Kumaoka, H., Biosynthesis of pyridoxine: origin of the nitrogen atom of pyridoxine in microorganisms. J. Nutr. Sci. Vitaminol., 46, 55-57 (2000).
36. Kaplan, J. B., Merkel, W. K., and Nichols, B. P., Evolution of glutamine amidotransferase genes: nucleotide sequences of the pabA genes from Salmonella typhimurium, Klebsiella aerogenes and Serratia marcescens. J. Mol. Biol., 183, 327-340 (1985).
37. Kane, J. F., Regulation of a common amidotran-sferase subunit. J. Bacteriol., 132, 419-425 (1977).