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Volumn 61, Issue 23, 1996, Pages 8010-8015

Cuprate-mediated synthesis and biological evaluation of cyclopropyl- and tert-butylfarnesyl diphosphate analogs

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; PROTEIN FARNESYLTRANSFERASE; TERPENOID;

EID: 0029823720     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614203     Document Type: Article
Times cited : (48)

References (51)
  • 11
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    • Cane, D. E. Chem. Rev. 1990, 90, 1089-1103.
    • (1990) Chem. Rev. , vol.90 , pp. 1089-1103
    • Cane, D.E.1
  • 15
    • 0027957905 scopus 로고
    • Peptide, and FPP-based photoaffinity labels have provided limited information about the PFTase active site: (a) Ying, W.; SeppLorenzino, L.; Cai, K.; Aloise, P.; Coleman, P. S. J. Biol. Chem 1994, 269, 470-477. (b) Bukhtiyarov, Y. E.; Omer, C. A.; Allen, C. M. J. Biol. Chem. 1995, 270, 19035-19040.
    • (1994) J. Biol. Chem , vol.269 , pp. 470-477
    • Ying, W.1    Sepplorenzino, L.2    Cai, K.3    Aloise, P.4    Coleman, P.S.5
  • 16
    • 0029111494 scopus 로고
    • Peptide, and FPP-based photoaffinity labels have provided limited information about the PFTase active site: (a) Ying, W.; SeppLorenzino, L.; Cai, K.; Aloise, P.; Coleman, P. S. J. Biol. Chem 1994, 269, 470-477. (b) Bukhtiyarov, Y. E.; Omer, C. A.; Allen, C. M. J. Biol. Chem. 1995, 270, 19035-19040.
    • (1995) J. Biol. Chem. , vol.270 , pp. 19035-19040
    • Bukhtiyarov, Y.E.1    Omer, C.A.2    Allen, C.M.3
  • 18
    • 0029983874 scopus 로고    scopus 로고
    • For another recent mechanistic study on PFTase (determination of its stereochemical course), see: Mu, Y. Q.; Omer, C. A.; Gibbs, R. A. J. Am. Chem. Soc. 1996, 118, 1817-1823.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1817-1823
    • Mu, Y.Q.1    Omer, C.A.2    Gibbs, R.A.3
  • 22
    • 0028191833 scopus 로고
    • Conversely, Cane and co-workers have recently shown that 12-vinyl FPP is a mechanism-based inhibitor of aristolochene synthase, but the corresponding cyclopropyl derivative is not: Cane, D. E.; Bryant, C. J. Am. Chem. Soc. 1994, 116, 12063-12064.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12063-12064
    • Cane, D.E.1    Bryant, C.2
  • 36
    • 85022440942 scopus 로고
    • (e) For a structural study on lower order cyanocuprates, see: Bertz, S. H. J. Am. Chem. Soc. 1991, 113, 5470-5471.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5470-5471
    • Bertz, S.H.1
  • 37
    • 16144366158 scopus 로고    scopus 로고
    • note
    • 29b emphasizing the very reactive nature of vinyl triflate 8.
  • 46
    • 16144366132 scopus 로고    scopus 로고
    • note
    • All synthetic reagents were from Aldrich Chemical Co. Solvents were from Aldrich or Fisher Scientific and were used as received unless otherwise indicated. HPLC work was carried out with HPLC grade solvents.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.