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Volumn 61, Issue 17, 1996, Pages 5932-5938

Twisted amides as selective acylating agents for hydroxyl groups under neutral conditions: Models for activated peptides during enzymatic acyl transfer reaction

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EID: 0001738245     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522015     Document Type: Article
Times cited : (78)

References (35)
  • 2
    • 0003438540 scopus 로고
    • Cornell University Press: Ithaca, NY
    • Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960. Robin, M. B.; Bovey, F. A.; Basch, H. In The Chemistry of Amides; Zabicky, J.,Ed.; Wiley-Interscience: London, 1970; pp 1-72.
    • (1960) The Nature of the Chemical Bond
    • Pauling, L.1
  • 3
    • 0002233130 scopus 로고
    • Zabicky, J.,Ed.; Wiley-Interscience: London
    • Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960. Robin, M. B.; Bovey, F. A.; Basch, H. In The Chemistry of Amides; Zabicky, J.,Ed.; Wiley-Interscience: London, 1970; pp 1-72.
    • (1970) The Chemistry of Amides , pp. 1-72
    • Robin, M.B.1    Bovey, F.A.2    Basch, H.3
  • 5
    • 0001261805 scopus 로고
    • Boyer, P. D.; Lardy, H.; Myrback, K., Eds.; Academic Press: New York
    • (a) Lumry, R. The Enzymes; Boyer, P. D.; Lardy, H.; Myrback, K., Eds.; Academic Press: New York, 1959; p 157.
    • (1959) The Enzymes , pp. 157
    • Lumry, R.1
  • 6
    • 0003035923 scopus 로고
    • Kaplan, N. O.; Kennedy, E. P., Eds.; Academic Press: New York
    • (b) Jencks, P. W. Current Aspects of Biochemical Energetics; Kaplan, N. O.; Kennedy, E. P., Eds.; Academic Press: New York, 1966; p 273.
    • (1966) Current Aspects of Biochemical Energetics , pp. 273
    • Jencks, P.W.1
  • 9
    • 0004135644 scopus 로고
    • Freeman and Company: New York, Chapter 2
    • (e) Walsh, C. Enzymatic Reaction Mechanisms; Freeman and Company: New York, 1979; Chapter 2, pp 24-48.
    • (1979) Enzymatic Reaction Mechanisms , pp. 24-48
    • Walsh, C.1
  • 14
    • 85033855567 scopus 로고    scopus 로고
    • note
    • Improved method for the synthesis of 2 was described in Experimental Section.
  • 16
    • 0000720944 scopus 로고
    • Brown and his co-workers have studied the hydrolysis of bicyclic distorted amides as models for activated peptide N-C=O units produced during enzyme-catalyzed hydrolysis, see: Somayaji, V.; Brown, R. S. J. Org. Chem. 1986, 51, 2676. Wang, P. Q.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757.
    • (1986) J. Org. Chem. , vol.51 , pp. 2676
    • Somayaji, V.1    Brown, R.S.2
  • 17
    • 0001245769 scopus 로고
    • Brown and his co-workers have studied the hydrolysis of bicyclic distorted amides as models for activated peptide N-C=O units produced during enzyme-catalyzed hydrolysis, see: Somayaji, V.; Brown, R. S. J. Org. Chem. 1986, 51, 2676. Wang, P. Q.; Bennet, A. J.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 5757.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5757
    • Wang, P.Q.1    Bennet, A.J.2    Brown, R.S.3    Santarsiero, B.D.4
  • 18
    • 85033848341 scopus 로고    scopus 로고
    • note
    • For a preliminary communication, see: ref 7.
  • 20
    • 4243089087 scopus 로고
    • Compound 1: Chung-shi, L.; Yuen-hwa, Y.; Yao, L.; Yong-jun, L.; Ai-hsueh, L.; Chi-yi, H. Tetrahedron Lett., 1981, 22, 3467. Compound 2: see refs 6 and 8. Compound 3: Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 53, 555.
    • (1979) Bull. Chem. Soc. Jpn. , vol.53 , pp. 555
    • Izawa, T.1    Mukaiyama, T.2


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