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Volumn 131, Issue 18, 2009, Pages 6332-6333

Biosynthesis of the sesquiterpene antibiotic albaflavenone in streptomyces coelicolor. mechanism and stereochemistry of the enzymatic formation of epi-isozizaene

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE RESIDUES; BINDING DOMAIN; CATALYZED OXIDATION; CYTOCHROME P450; DEUTERATIONS; ENZYMATIC FORMATION; FARNESYL DIPHOSPHATE; GC-MS ANALYSIS; METHYL MIGRATIONS; MULTI-STEP; MUTANT PROTEINS; SESQUITERPENES; SITE DIRECTED MUTAGENESIS; STREPTOMYCES COELICOLOR; SYNTHASES; WILD TYPES;

EID: 69949157277     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901313v     Document Type: Article
Times cited : (78)

References (19)
  • 5
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    • Cane, D. E.; Ha, H. J. J. Am. Chem. Soc. 1988, 110, 6865-6870. Cane, D. E.; Ha, H. J. J. Am. Chem. Soc. 1986, 108, 3097-3099.
    • Cane, D. E.; Ha, H. J. J. Am. Chem. Soc. 1988, 110, 6865-6870. Cane, D. E.; Ha, H. J. J. Am. Chem. Soc. 1986, 108, 3097-3099.
  • 7
    • 84869611195 scopus 로고    scopus 로고
    • Incubation of (3RS)-NPP gave an ̃1:1 mixture of epi-isozizaene (3) and β-farnesene (9). Control experiments showed that >95% of this coproduct 9 was derived from the unnatural enantiomer (3S)-NPP, indicating that only (3R)-NPP can be cyclized by epi-isozizaene synthase.
    • Incubation of (3RS)-NPP gave an ̃1:1 mixture of epi-isozizaene (3) and β-farnesene (9). Control experiments showed that >95% of this coproduct 9 was derived from the unnatural enantiomer (3S)-NPP, indicating that only (3R)-NPP can be cyclized by epi-isozizaene synthase.
  • 9
    • 0025102529 scopus 로고    scopus 로고
    • 3]FPP (2d).
    • 3]FPP (2d).
  • 10
    • 70149115690 scopus 로고    scopus 로고
    • The stereochemistry of the H-4 bridgehead-proton in 6, 7, and 8 was deduced based on the assumption of least motion of the 2-propyl cation side chain during the formation of the new C-C bond in 7.
    • The stereochemistry of the H-4 bridgehead-proton in 6, 7, and 8 was deduced based on the assumption of least motion of the 2-propyl cation side chain during the formation of the new C-C bond in 7.
  • 11
    • 33646153062 scopus 로고    scopus 로고
    • For analogous sequential 1,2-methyl migration and syn-deprotonation, cf. aristolochene synthase (ref 3a) and epi-aristolochene synthase
    • For analogous sequential 1,2-methyl migration and syn-deprotonation, cf. aristolochene synthase (ref 3a) and epi-aristolochene synthase: Schenk, D. J.; Starks, C. M.; Manna, K. R.; Chappell, J.; Noel, J. P.; Coates, R. M. Arch. Biochem. Biophys. 2006, 448, 31-44.
    • (2006) Arch. Biochem. Biophys , vol.448 , pp. 31-44
    • Schenk, D.J.1    Starks, C.M.2    Manna, K.R.3    Chappell, J.4    Noel, J.P.5    Coates, R.M.6
  • 13
    • 70149107510 scopus 로고    scopus 로고
    • The absolute configurations of 10-13 and 15 were provisionally assigned on the basis of the cyclization mechanism and the known absolute configuration of epi-isozizaene.
    • The absolute configurations of 10-13 and 15 were provisionally assigned on the basis of the cyclization mechanism and the known absolute configuration of epi-isozizaene.
  • 15
    • 34548851139 scopus 로고    scopus 로고
    • Trichodiene synthase: Vedula, L. S.; Zhao, Y.; Coates, R. M.; Koyama, T.; Cane, D. E.; Christianson, D. W. Arch. Biochem. Biophys. 2007, 466, 260-266.
    • Trichodiene synthase: Vedula, L. S.; Zhao, Y.; Coates, R. M.; Koyama, T.; Cane, D. E.; Christianson, D. W. Arch. Biochem. Biophys. 2007, 466, 260-266.
  • 16
    • 0037014703 scopus 로고    scopus 로고
    • Pentalenene synthase: Seemann, M.; Zhai, G.; de Kraker, J. W.; Paschall, C. M.; Christianson, D. W.; Cane, D. E. J. Am. Chem. Soc. 2002, 124, 7681-7689.
    • Pentalenene synthase: Seemann, M.; Zhai, G.; de Kraker, J. W.; Paschall, C. M.; Christianson, D. W.; Cane, D. E. J. Am. Chem. Soc. 2002, 124, 7681-7689.
  • 17
    • 2942558483 scopus 로고    scopus 로고
    • Aristolochene synthase: Felicetti, B.; Cane, D. E. J. Am. Chem. Soc. 2004, 126, 7212-7221.
    • Aristolochene synthase: Felicetti, B.; Cane, D. E. J. Am. Chem. Soc. 2004, 126, 7212-7221.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.