Identification and characterization of gerPI and gerPII involved in epoxidation and hydroxylation of dihydrochalcolactone in Streptomyces species KCTC 0041BP

Archives of Microbiology

Volumn 193, Issue 2, 2011, Pages 95-103

  Malla, Sailesh ^a   Thuy, Ta Thi Thu ^a   Oh, Tae Jin ^a   Sohng, Jae Kyung ^a  

^a SunMoon University   (South Korea)

Author keywords

Cytochrome P450; Dihydrochalcomycin; Epoxidation; Gene disruption; Hydroxylation; Streptomyces

Indexed keywords

12,13 DE EPOXYDIHYDROCHALCOMYCIN; 8 DEHYDROXY 12,13 DE EPOXYDIHYDROCHALCOMYCIN; ANTIBIOTIC AGENT; CYTOCHROME P450; CYTOCHROME P450 GERPI; CYTOCHROME P450 GERPII; DIHYDROCHALCOMYCIN; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; COMPUTER MODEL; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ANALYSIS; EPOXIDATION; GENE CLUSTER; GENE DISRUPTION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE ANALYSIS; STREPTOMYCES; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; GLYCOSIDES; HYDROXYLATION; MACROLIDES; MOLECULAR SEQUENCE DATA; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES SP. KCTC 0041BP;

EID: 79251649090     PISSN: 03028933     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00203-010-0648-7     Document Type: Article

References (31)

1. JF Andersen CR Hutchinson 1992 Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase J Bacteriol 174 725 735 1:CAS:528:DyaK3sXisFSntLk%3D 1732208
2. JF Anderson K Tatsuta H Gunji T Ishiyama CR Hutchinson 1993 Substrate specificity of 6-deoxyerythronolide B hydroxylase, a bacterial cytochrome P450 of erythromycin A biosynthesis Biochemistry 32 1905 1913 10.1021/bi00059a004
3. Y Anzai S Li MR Chaulagain K Kinoshita F Kato J Montgomery DH Sherman 2008 Functional analysis of MycCI and MycG, cytochrome P450 enzymes involved in biosynthesis of mycinamicin macrolide antibiotics Chem Biol 15 950 959 1:CAS:528:DC%2BD1cXhtFCnsr3L 10.1016/j.chembiol.2008.07.014 18804032
4. RN Asolkar RP Maskey E Helmke H Laatsch 2002 Chalcomycin B, a new macrolide antibiotic from the marine isolate Streptomyces sp. B7064 J Antibiot 55 893 898 1:CAS:528:DC%2BD38XotlChs78%3D 12523822
5. M Bierman R Logan K O'Brien ET Seno RN Rao BE Schoner 1992 Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp Gene 116 43 49 1:CAS:528:DyaK38XltVGgt74%3D 10.1016/0378-1119(92)90627-2 1628843
6. JR Cupp-Vickery H Li TL Poulos 1994 Preliminary crystallographic analysis of an enzyme involved in erythromycin biosynthesis: cytochrome P450eryF Proteins 20 197 201 1:CAS:528:DyaK2MXhvFGktrY%3D 10.1002/prot.340200210 7846029
7. F Denis R Brzezinski 1991 An improved aminoglycoside resistance gene cassette for use in gram-negative bacteria and Streptomyces FEMS Microbiol Lett 65 261 264 1:STN:280:DyaK38%2FgvFWitw%3D%3D 10.1111/j.1574-6968.1991.tb04769.x 1655560
8. YM Goo YY Lee BT Kim 1997 A new 16-membered chalcomycin type macrolide antibiotic, 250-144C J Antibiot 50 85 88 1:CAS:528:DyaK2sXisV2msLw%3D 9066771
9. S Graham-Lorence JA Peterson 1996 P450s: structural similarities and functional differences FASEB J 10 206 214 1:CAS:528:DyaK28XhsFOrt7c%3D 8641554
10. FP Guengerich 1991 Reactions and significance of cytochrome P-450 enzymes J Biol Chem 266 10019 10022 1:CAS:528:DyaK3MXksVClu7o%3D 2037557
11. Ikeda H, Omura S (2002) Biosynthesis, regulation and genetics of macrolide production. In: Omura S (ed) Macrolide antibiotics. Chemistry, biology and practice, 2nd edn. Academic Press, New York, pp 286-320
12. BP Jaishy SK Lim ID Yoo JC Yoo JK Sohng DH Nam 2006 Cloning and characterization of a gene cluster for the production of polyketide macrolide dihydrochalcomycin in Streptomyces sp. KCTC 0041BP J Microbiol Biotechnol 16 764 770 1:CAS:528:DC%2BD28Xms1Omsrs%3D
13. Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hopwood DA (2000) Practical Streptomyces genetics. The John Innes Centre Foundation, Norwich
14. SD Kim IJ Ryoo CJ Kim WG Kim JP Kim JY Kong H Koshino M Uramoto ID Yoo 1996 GERI-155 a new macrolide antibiotic related to chalcomycin J Antibiot 49 955 957 1:CAS:528:DyaK28XlvFahsrw%3D 8931736
15. K Kinoshita S Takenaka H Suzuki T Morohoshi M Hayashi 1992 Mycinamicins, new macrolide antibiotics. XIII. Isolation and structures of novel fermentation products from Micromonospora griseorubida (FERM BP-705) J Antibiot 45 1 9 1:CAS:528:DyaK38XhsVOlurw%3D 1548179
16. DC Lamb T Skaug HL Song CJ Jackson LM Podust MR Waterman DB Kell DE Kelly SL Kelly 2002 The Cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2) J Biol Chem 277 24000 24005 1:CAS:528:DC%2BD38XltlOiurw%3D 10.1074/jbc.M111109200 11943767
17. DC Lamb H Ikeda DR Nelson J Ishikawa T Skaug C Jackson S Omura MR Waterman SL Kelly 2003 Cytochrome P450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2) Biochem Biophys Res Commun 307 610 619 1:CAS:528:DC%2BD3sXlvVCrs7k%3D 10.1016/S0006-291X(03)01231-2 12893267
18. SK Lee DB Basnet CY Choi JK Sohng JS Ahn YJ Yoon 2004 The role of erythromycin C-12 hydroxylase Ery, as a substitute for PikC hydroxylase in pikromycin biosynthesis Bioorg Chem 32 549 559 1:CAS:528:DC%2BD2cXpsVOltLk%3D 10.1016/j.bioorg.2004.06.002 15530995
19. DJ MacNeil KM Gewain CL Ruby G Dezeny PH Gibbons T MacNeil 1992 Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector Gene 111 61 68 1:CAS:528:DyaK38XisV2ls7s%3D 10.1016/0378-1119(92)90603-M 1547955
20. MV Mendes E Recio R Fouces R Luiten JF Martin JF Aparicio 2001 Engineered biosynthesis of novel polyenes: a pimaricin derivative produced by targeted gene disruption in Streptomyces natalensis Chem Biol 8 635 644 1:CAS:528:DC%2BD3MXltVGjurc%3D 10.1016/S1074-5521(01)00033-3 11451665
21. DR Nelson T Kamataki DJ Waxman FP Guengerich RW Estabrook R Feyereisen FJ Gonzalez MJ Coon IC Gunsalus O Gotoh, et al. 1993 The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature DNA Cell Biol 12 1 51 1:CAS:528:DyaK3sXhsVSktLk%3D 10.1089/dna.1993.12.1 7678494
22. Y Ohnishi J Ishikawa H Hara H Suzuki M Ikenoya H Ikeda A Yamashita M Hattori S Horinouchi 2008 Genome sequence of the streptomycin-producing microorganism Streptomyces griseus IFO 13350 J Bacterol 190 4050 4060 1:CAS:528:DC%2BD1cXmsVOmsbg%3D 10.1128/JB.00204-08
23. N Parajuli DB Basnet HC Lee JK Sohng K Liou 2004 Genome analyses of Streptomyces peucetius ATCC 27952 for the identification and comparison of cytochrome P450 complement with other Streptomyces Arch Biochem Biophys 425 233 241 1:CAS:528:DC%2BD2cXjsVWmsbk%3D 10.1016/j.abb.2004.03.011 15111132
24. AM Rodriguez C Olano C Méndez CR Hutchinson JA Salas 1995 A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis by Streptomyces antibioticus FEMS Microbiol Lett 127 117 120 1:CAS:528: DyaK2MXksVyrtrg%3D 10.1111/j.1574-6968.1995.tb07459.x 7737473
25. R Spagnoli L Cappelletti L Toscano 1983 Biological conversion of erythronolide B, an intermediate of erythromycin biogenesis, into new hybrid macrolide antibiotics J Antibiot 36 365 375 1:CAS:528:DyaL3sXktlGku7s%3D 6343328
26. D Stassi S Donadio MJ Staver L Katz 1993 Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis J Bacteriol 175 182 189 1:CAS:528:DyaK3sXkvVOrsb0%3D 8416893
27. L Tang S Shah L Chung J Carney L Katz C Khosla B Julien 2000 Cloning and heterologous expression of the epothilone gene cluster Science 287 640 642 1:CAS:528:DC%2BD3cXovVOrtQ%3D%3D 10.1126/science.287.5453.640 10649995
28. SL Ward Z Hu A Schirmer R Reid WP Revill CD Reeves OV Petrakovsky SD Dong L Katz 2004 Chalcomycin biosynthesis gene cluster from Streptomyces bikiniensis: novel features of an unusual ketolide produced through expression of the chm polyketide synthase in Streptomyces fradiae Antimicrob Agents Chemother 48 4703 4712 1:CAS:528:DC%2BD2cXhtVKmt7%2FN 10.1128/AAC.48.12.4703- 4712.2004 15561847
29. D Werck-Reichhart R Feyereisen 2000 Cytochromes P450: a success story Genome Biol 1 3003.1 3003.9 10.1186/gb-2000-1-6-reviews3003
30. PWK Woo JR Rubin 1996 Chalcomycin: single-crystal X-ray crystallographic analysis; biosynthetic and stereochemical correlations with polyoxo macrolide antibiotics Tetrahedron 52 3857 3872 1:CAS:528:DyaK28Xhs12ks7o%3D 10.1016/S0040-4020(96)00052-X
31. Y Xue D Wilson L Zhao H-W Liu DH Sherman 1998 Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae Chem Biol 5 661 667 1:CAS:528:DyaK1cXotVWksrY%3D 10.1016/S1074-5521(98)90293-9 9831532