Substrate specificity of 2-deoxy-scyllo-inosose synthase, the starter enzyme for 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates and proposed mechanism

Bioscience, Biotechnology and Biochemistry

Volumn 62, Issue 12, 1998, Pages 2396-2407

  Iwase, Noriaki ^a   Kudo, Fumitaka ^a   Yamauchi, Noriaki ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

2 deoxy scyllo inosose synthase; 2 deoxystreptamine biosynthesis; Aminocyclitol antibiotic; Deoxyglucose 6 phosphates; Dide oxyinososes

Indexed keywords

2 DEOXY SCYLLO INOSOSE SYNTHASE; 2 DEOXYINOSOSE; 2 DEOXYSTREPTAMINE; 2-DEOXY-SCYLLO-INOSOSE SYNTHASE; 2-DEOXYGLUCOSE-6-PHOSPHATE; 2-DEOXYINOSOSE; 2-DEOXYSTREPTAMINE; DEOXYGLUCOSE 6 PHOSPHATE; DRUG DERIVATIVE; GLUCOSE 6 PHOSPHATE; HEXOSAMINE; INOSITOL; LYASE;

ARTICLE; BIOSYNTHESIS; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLUCOSE-6-PHOSPHATE; HEXOSAMINES; INOSITOL; LYASES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUBSTRATE SPECIFICITY;

EID: 0032249041     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.2396     Document Type: Article

References (17)

1. Kudo, F., Yamauchi, N., Suzuki, R., and Kakinuma, K., Kinetic isotope effect and reaction mechanism of 2-deoxy-scyllo-m-osose synthase derived from butirosin-producing Bacillus circulars. J. Antibiot., 50, 424-428, (1997).
2. 13C]glucose into neomycin. J. Am. Chem. Soc., 96, 2263-2265 (1974).
3. Daum, S. J., Rosi, D., and Goss, W. A., Mutational biosynthesis by idiotrophs of Micromonospora purpurea. II. Conversion of nonamino-containing cyclitols to aminoglycoside antibiotics. J. Antibiot., 30, 98-105 (1977).
4. 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. Antibiot., 32, 891-899 (1979).
5. Fujiwara, T., Takahashi, Y., Matsumoto, K., and Kondo, E., Isolation of an intermediate of 2-deoxystreptamine biosynthesis from a mutant of Bacillus circulons. J. Antibiot., 33, 824-829 (1980).
6. Kase, H., Iida, T., Odakura, Y., Shirahata, K., and Nakayama, K., Accumulation of 2-deoxy-scyllo-inosamine by a 2-deoxys-treptamine-requiring idiotroph of Micromonospora sagamien-sis. J. Antibiot., 33, 1210-1212 (1980).
7. Yamauchi, N., and Kakinuma, K., Confirmation of in vitro synthesis of 2-deoxy-scyllo-inosose, the earliest intermediate in the biosynthesis of 2-deoxystreptamine, using cell free preparations of Streptomyces fradiae. J. Antibiot., 45, 774-780 (1992).
8. Yamauchi, N., and Kakinuma, K., Enzymatic carbocycle formation in microbial secondary metabolism. The mechanism of 2-deoxy-scyllo-inosose synthase reaction as a crucial step in the 2-deoxystreptamine biosynthesis in Streptomyces fradiae. J. Org. Chem., 60, 5614-5619 (1995).
9. Shaw, K. J., Rather, P. N., Hare, R. S., and Miller, G. H., Molecular genetics of aminoglycoside resistance genes and familial relationships of the aminoglycoside-modifying enzymes. Microbiol. Rev., 57, 138-163 (1993).
10. Kiddle, J. J., Quebrachitol: A versatile building block in the construction of naturally occurring bioactive materials. Chem. Rev., 95, 2189-2202 (1995).
11. Garegg, P. J., Iversen, T., Johansson, R., and Lindberg, B., Synthesis of some mono-O-benzyl- and penta-O-methyl-myo-in-ositols. Carbohydr. Res., 130, 322-326 (1984).
12. Barton, D. H. R., and McCombie, S. W., A new method for the deoxygenation of secondary alcohols. J. Chem. Soc. Perkin I, 1574-1585 (1975).
13. Tipson, R. S., and Cohen, A., Action of zinc dust and sodium iodide in A^ZV-dimethylformamide on contiguous, secondary sul-fonyloxy groups: a simple method for introducing nonterminal unsaturation. Carbohydr. Res., 1, 338-340 (1965).
14. 2]-2-deoxy-5-cyZZo-inosose. J. Antibiot., 45, 756-766 (1992).
15. Lardy, H. A., and Fischer, H. O. L., Phosphoric esters of biological importance I. The synthesis of glucose-6-phosphate. J. Biol. Chem., 164, 513-519 (1946).
16. Petrakova, E., and Glaudemans, C. P. J., Synthesis of the methyl a-glycoside of some isomalto-oligosaccharides specifically deoxygenated at position C-4. Carbohydr. Res., 279, 133-150 (1995).
17. Bell, D. J., and Lorber, J., Use of the benzyl radical in synthesis of methylated sugars. Part I. 4:6-Dimethyl glucose. J. Chem. Soc., 453-455 (1940).