Biosynthesis of 2-deoxystreptamine-containing antibiotics in Streptoalloteichus hindustanus JCM 3268: Characterization of 2-deoxy-scyllo-inosose synthase

Journal of Antibiotics

Volumn 59, Issue 6, 2006, Pages 358-361

  Hirayama, Toshifumi ^a   Tamegai, Hideyuki ^a,b   Kudo, Fumitaka ^a   Kojima, Kazumasa ^a   Kakinuma, Katsumi ^a   Eguchi, Tadashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b NIHON UNIVERSITY   (Japan)

Author keywords

2 deoxy scyllo inosose synthase; 2 deoxystreptamine biosynthetic genes; Kinetics; Streptoalloteichus hindustanus

Indexed keywords

2 DEOXYSCYLLO INOSOSE SYNTHASE; 2 DEOXYSTREPTAMINE; ANTIBIOTIC AGENT; APRAMYCIN; GENTAMICIN; HYGROMYCIN; ISTAMYCIN; KANAMYCIN; LIVIDOMYCIN; NEOMYCIN; PAROMOMYCIN; RIBOSTAMYCIN; SYNTHETASE; TOBRAMYCIN; UNCLASSIFIED DRUG;

ALLOH GENE; ARTICLE; BIOCHEMISTRY; BIOSYNTHESIS; CONTROLLED STUDY; ENZYME ACTIVITY; GENE; GENE CLUSTER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PSEUDONOCARDIACEAE; STREPTOALLOTEICHUS HINDUSTANUS;

ACTINOMYCETALES; ANTI-BACTERIAL AGENTS; HEXOSAMINES; LYASES; MULTIGENE FAMILY;

STREPTOALLOTEICHUS HINDUSTANUS;

EID: 33746909870     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2006.51     Document Type: Article

References (21)

1. Litovchick A, Lapidot A, Eisenstein M, Kalinkovich A, Borkow G. Neomycin B-arginine conjugate, a novel HIV-1 Tat antagonist: synthesis and anti-HIV activities. Biochemistry 40: 15612-15623 (2001)
2. Lapidot A, Vijayabaskar V, Litovchick A, Yu J, James TL. Structure-activity relationships of aminoglycoside-arginine conjugates that bind HIV-1 RNAs as determined by fluorescence and NMR spectroscopy. FEBS Lett 577: 415-421 (2004)
3. Kudo F, Tamegai H, Fujiwara T, Tagami U, Hirayama K, 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 dehydroquinate synthase. J Antibiot 52: 559-571 (1999)
4. Ota Y, Tamegai H, Kudo F, Kuriki H, Koike-Takeshita A, Eguchi T, Kakinuma K. Butirosin-biosynthetic gene cluster from Bacillus circulans. J Antibiot 53: 1158-1167 (2000)
5. Kudo F, Numakura M, Tamegai H, Yamamoto H, Eguchi T, Kakinuma K. Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulons SANK 72073. J Antibiot 58: 373-379 (2005)
6. Kharel MK, Basnet DB, Lee HC, Liou K, Woo JS, Kim BG, Sohng JK. Isolation and characterization of the tobramycin biosynthetic gene cluster from Streptomyces tenebrarius. FEMS Microbiol Lett 230: 185-190 (2004)
7. Yanai K, Murakami T. The kanamycin biosynthetic gene cluster from Streptomyces kanamyceticus. J Antibiot 57: 351-354 (2004)
8. Kharel MK, Subba B, Basnet DB, Woo JS, Lee HC, Liou K, Sohng JK. A gene cluster for biosynthesis of kanamycin from Streptomyces kanamyceticus: comparison with gentamicin biosynthetic gene cluster. Arch Biochem Biophys 429: 204-214 (2004)
9. Huang F, Haydock SF, Mironenko T, Spiteller D, Li Y, Spencer JB. The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: characterisation of an aminotransferase involved in the formation of 2-deoxystreptamine. Org Biomol Chem 3: 1410-1418 (2005)
10. Kudo F, Yamamoto Y, Yokoyama K, Eguchi T, Kakinuma K. Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC12773. J Antibiot 58: 766-774 (2005)
11. Subba B, Kharel MK, Lee HC, Liou K, Kim B-G, Sohng JK. The ribostamycin biosynthetic gene cluster in Streptomyces ribosidificus: comparison with butirosin biosynthesis. Mol Cells 20: 90-96 (2005)
12. Unwin J, Standage S, Alexander D, Hosted T Jr, Horan AC, Wellington EMH. Gene cluster in Micromonospora echinospora ATCC15835 for the biosynthesis of the gentamicin C complex. J Antibiot 57: 436-445 (2004)
13. Kharel MK, Basnet DB, Lee HC, Liou K, Moon YH, Kim J-J, Woo JS, Sohng JK. Molecular cloning and characterization of a 2-deoxystreptamine biosynthetic gene cluster in gentamicin-producing Micromonospora echinospora ATCC15835. Mol Cells 18: 71-78 (2004)
14. Tomita K, Uenoyama Y, Numata K, Sasahira T, Hoshino Y, Fujisawa K, Tsukiura H, Kawaguchi H. Streptoalloteichus, a new genus of the family Actinoplanaceae. J Antibiot 31: 497-510 (1978)
15. Yokoyama K, Kudo F, Kuwahara M, Inomata K, Tamegai H, Eguchi T, Kakinuma K. Stereochemical recognition of doubly functional aminotransferase in 2-deoxystreptamine biosynthesis. J Am Chem Soc 127: 5869-5874 (2005)
16. Ahlert J, Distler J, Mansouri K, Piepersberg W. Identification of stsC, the gene encoding the L-glutamine: scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes. Arch Microbiol 168: 102-113 (1997)
17. Tamegai H, Eguchi T, Kakinuma K. First identification of Streptomyces genes involved in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics-genetic and evolutionary analysis of L-glutamine: 2-deoxy-scyllo-inosose aminotransferase genes. J Antibiot 55: 1016-1018 (2002)
18. Kakinuma K, Nango E, Kudo F, Matsushima Y, Eguchi T. An expeditious chemo-enzymatic route from glucose to catechol by the use of 2-deoxy-scyllo-inosose synthase. Tetrahedron Lett 41: 1935-1938 (2000)
19. Nango E, Eguchi T, Kakinuma K. 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. J Org Chem 69: 593-600 (2004)
20. Carpenter EP, Hawkins AR, Frost JW, Brown KA. Structure of dehydroquinate synthase reveals an active site capable of multistep catalysis. Nature 394: 299-302 (1998)
21. Eguchi T, Sasaki S, Huang Z, Kakinuma K. Importance of specific hydrogen-bond donor-acceptor interactions for the key carbocycle-forming reaction catalyzed by 2-deoxy-scyllo-inosose synthase in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics. J Org Chem 67: 3979-3984 (2002)