Active Site Mapping of 2-Deoxy-scyllo-inosose Synthase, the Key Starter Enzyme for the Biosynthesis of 2-Deoxystreptamine. Mechanism-Based Inhibition and Identification of Lysine-141 As the Entrapped Nucleophile

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 593-600

  Nango, Eriko ^a   Eguchi, Tadashi ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; ENZYME INHIBITION; GLUCOSE;

MOLECULAR MASS;

ENZYMES;

2 DEOXY SCYLLO INOSOSE SYNTHASE; 2 DEOXYSTREPTAMINE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; CARBAGLUCOSE 6 PHOSPHATE; CARBONYL DERIVATIVE; CHYMOTRYPSIN; DEHYDROQUINATE SYNTHASE; ENZYME INHIBITOR; GLUCOSE 6 PHOSPHATE; LYSINE; SYNTHETASE; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; BACILLUS CIRCULANS; CONTROLLED STUDY; COVALENT BOND; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; ESCHERICHIA COLI; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICHAEL ADDITION; MOLECULAR WEIGHT; NONHUMAN; REACTION ANALYSIS; STREPTOMYCES FRADIAE;

AMINO ACID SEQUENCE; BINDING SITES; ENZYME INHIBITORS; ESCHERICHIA COLI; GLUCOSE; HEXOSAMINES; LYASES; LYSINE; MASS SPECTROMETRY; MOLECULAR WEIGHT; PEPTIDE FRAGMENTS; PEPTIDE MAPPING; RECOMBINANT PROTEINS;

EID: 0842328952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034706y     Document Type: Article

References (32)

1. Rinehart, K. L., Jr.; Stroshane, R. M. J. Antibiot. 1976, 29, 319-353.
2. Rinehart, K. L., Jr.; Suami, T., Eds. Aminocyclitol antibiotics; ACS Symp. Ser., No. 125; American Chemical Society: Washington, DC, 1980.
3. Shier, W. T.; Rinehart, K. L., Jr.; Gottlieb, D. Proc. Natl. Acad. Sci. U.S.A. 1969, 63, 198-204.
4. Nagaoka, K.; Demain, A. L. J. Antibiot. 1975, 28, 627-635.
5. Daum, S. J.; Rosi, D.; Goss, W. A. J. Am. Chem. Soc. 1977, 99, 283-284.
6. Daum, S. J.; Rosi, D.; Goss, W. A. J. Antibiot. 1977, 30, 98-105.
7. Furumai, T.; Takeda, K.; Kinumaki, A.; Ito, Y.; Okuda, T. J. Antibiot. 1979, 32, 891-899.
8. Kase, H.; Iida, T.; Odakura, Y.; Shirahata, K.; Nakayama, K. J. Antibiot. 1980, 33, 1210-1212.
9. Fujiwara, T.; Takahashi, Y.; Matsumoto, K.; Kondo, E. J. Antibiot. 1980, 33, 824-829.
10. Fujiwara, T.; Takahashi, Y.; Matsumoto, K.; Kondo, E. J. Antibiot. 1980, 33, 836-841.
11. Kakinuma, K.; Ogawa, Y.; Sasaki, T.; Seto, H.; Otake, N. J. Am. Chem. Soc. 1981, 103, 5614-5616.
12. Kakinuma, K.; Ogawa, Y.; Sasaki, T.; Seto, H.; Otake, N. J. Antibiot. 1989, 42, 926-933.
13. Yamauchi, N.; Kakinuma, K. J. Antibiot. 1992, 45, 767-773.
14. Yamauchi, N.; Kakinuma, K. J. Antibiot. 1992, 45, 774-780.
15. Yamauchi, N.; Kakinuma, K. J. Org. Chem. 1995, 60, 5614-5619.
16. Kudo, F.; Yamauchi, N.; Suzuki, R.; Kakinuma, K. J. Antibiot. 1997, 50, 424-428.
17. Yamauchi, N.; Kakinuma, K. J. Antibiot. 1993, 46, 1916-1918.
18. Nango, E.; Kudo, F.; Eguchi, T.; Kakinuma, K. Chem. Lett. 2003, 32, 438-439.
19. Kudo, F.; Hosomi, Y.; Tamegai, H.; Kakinuma, K. J. Antibiot. 1999, 52, 81-88.
20. Kudo, F.; Tamegai, H.; Fujiwara, T.; Tagami, U.; Hirayama, K.; Kakinuma, K. J. Antibiot. 1999, 52, 559-571.
21. Kakinuma, K.; Nango, E.; Kudo, F.; Matsushima, Y.; Eguchi, T. Tetrahedron Lett. 2000, 41, 1935-1938.
22. Hansen, C. A.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 5926-5927.
23. Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979-3984.
24. Silverman, R. B. Mechanism Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press Inc.: Boca Raton, FL, 1988.
25. Walsh, C. T. Annu. Rev. Biochem. 1984, 53, 493-535.
26. Ogawa, S.; Tsukiboshi, Y.; Iwasawa, Y.; Suami, T. Carbohydr. Res. 1985, 136, 77-89.
27. Yoshikawa, M.; Murakami, N.; Yokokawa, Y.; Inoue, Y.; Kuroda, Y.; Kitagawa, I. Tetrahedron 1994, 50, 9619-9628.
28. Entwistle, D. A.; Hudlicky, T. Tetrahedron Lett. 1995, 36, 2591-2594.
29. Yamauchi, N.; Kakinuma, K. J. Antibiot. 1992, 45, 756-766.
30. Kitz, R.; Wilson, I. B. J. Biol. Chem. 1962, 237, 3245.
31. Widlanski, T.; Bender, S. L.; Knowles, J. R. Biochemistry 1989, 28, 7572-7582.
32. Widlanski, T. S.; Bender, S. L.; Knowles, J. R. J. Am. Chem. Soc. 1987, 109, 1873-1875.