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Volumn 8, Issue 4, 1998, Pages 351-356

Thiophilic ring-opening and rearrangement reactions of epoxyketone natural products

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; EPOXYKETONE; GLUTATHIONE; KETONE DERIVATIVE; NATURAL PRODUCT; SCAVENGER; UNCLASSIFIED DRUG;

EID: 0032539635     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00026-2     Document Type: Article
Times cited : (41)

References (22)
  • 1
    • 0026725281 scopus 로고
    • 1. See, for example, Abelson, P. H. Science 1992, 256, 1609.
    • (1992) Science , vol.256 , pp. 1609
    • Abelson, P.H.1
  • 15
    • 0029037105 scopus 로고
    • (b) For a recent example for the use of thiols as models for assessment of the reactivity of antitumor antibiotics, see: Behroozi, S. J.; Kim, W.; Gates, K. S. J. Org. Chem. 1995, 60, 3964.
    • (1995) J. Org. Chem. , vol.60 , pp. 3964
    • Behroozi, S.J.1    Kim, W.2    Gates, K.S.3
  • 16
    • 0010602948 scopus 로고
    • Ph.D. Thesis, University of Pittsburgh
    • 12. The structure of 2 was confirmed by extensive NOE and decoupling experiments: Kim, Y.; Ph.D. Thesis, University of Pittsburgh, 1995.
    • (1995)
    • Kim, Y.1
  • 20
    • 0027849639 scopus 로고
    • 16. Natural product serine-protease inhibitors with α-keto arginine residues such as cyclotheonamide also occur prediminantly as hydrates in aqueous environment. In the enzyme active site, alkylation of the serine-159 side chain hydroxy group occurs presumably via the intermediate ketone: Lee, A. Y.; Hagihara, M.; Karmacharya, R.; Albers, M. W.; Schreiber, S. L.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 12619. Maryanoff, B. E.; Qiu, X. Y.; Padmanabhan, K. P.; Tulinsky, A.; Almond, H. R.; Andradegordon, P.; Greco, M. N.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A. J.; Brungs, P. H.; Fusetani, N. Proc. Nat. Acad. Sci. U.S.A. 1993, 90, 8048.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 12619
    • Lee, A.Y.1    Hagihara, M.2    Karmacharya, R.3    Albers, M.W.4    Schreiber, S.L.5    Clardy, J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.