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Volumn 44, Issue 37, 2003, Pages 6999-7002

New stereoselective synthesis of the peptidic aminopeptidase inhibitors bestatin, phebestin and probestin

Author keywords

Aminopeptidase inhibitors; Asymmetric synthesis; , epoxy esters

Indexed keywords

AMINOPEPTIDASE INHIBITOR; BESTATIN; ENZYME INHIBITOR; PHEBESTIN; PROBESTIN; UNCLASSIFIED DRUG;

EID: 0042659190     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01799-4     Document Type: Article
Times cited : (32)

References (21)
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    • Umezawa K., Ikeda Y., Uchihata Y., Naganawa H., Kondo S. J. Org. Chem. 65:2000;459; (b) Compound 5: Umezawa K., Nakazawa K.i, Ikeda Y., Naganawa H., Kondo S. J. Org. Chem. 64:1999;3034-3038. Harbeson S.L., Rich D.H. Biochemistry. 27:1988;7301.
    • (1988) Biochemistry , vol.27 , pp. 7301
    • Harbeson, S.L.1    Rich, D.H.2
  • 4
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    • Review:
    • Review: Bergmeier S.C. Tetrahedron. 56:2000;2561. Kolb H.C., Sharpless K.B. Beller M., Bolm C. Transition Metals for Organic Synthesis. 1998;243 Wiley-VCH, New York. (b) O'Brien P. Angew. Chem., Int. Ed. Engl. 1999,38, 326.
    • (2000) Tetrahedron , vol.56 , pp. 2561
    • Bergmeier, S.C.1
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    • 0033083525 scopus 로고    scopus 로고
    • Kolb H.C., Sharpless K.B. Beller M., Bolm C. Transition Metals for Organic Synthesis. 1998;243 Wiley-VCH, New York. (b) O'Brien P. Angew. Chem., Int. Ed. Engl. 1999,38, 326.
    • (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , pp. 326
    • O'Brien, P.1
  • 8
    • 0003821175 scopus 로고    scopus 로고
    • For most recent reviews covering the different aspects of the AE, see:
    • For most recent reviews covering the different aspects of the AE, see: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 1; (b) Katsuki., T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; Vol. II, p. 621.
    • (1996) Org. React. , pp. 1
    • Katsuki, T.1    Martin, V.S.2
  • 9
    • 0000345527 scopus 로고    scopus 로고
    • For most recent reviews covering the different aspects of the AE, see: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York
    • For most recent reviews covering the different aspects of the AE, see: (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 1; (b) Katsuki., T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; Vol. II, p. 621.
    • (1999) In Comprehensive Asymmetric Catalysis , vol.2 , pp. 621
    • Katsuki, T.1
  • 17
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    • Compound 5 was easily prepared by standard procedure (Ref. 7a) in four high yielding steps starting from the commercially available phenylacetaldehyde
    • Compound 5 was easily prepared by standard procedure (Ref. 7a) in four high yielding steps starting from the commercially available phenylacetaldehyde.
  • 18
    • 85031141373 scopus 로고    scopus 로고
    • 4NF in DMF
    • 4NF in DMF. In the case (a) the reaction was not stereoselective and in the cases (b) and (c) the starting material 3 remained unchanged when the reaction temperature was ∼60°C and decomposed when it was heated to 80-90°C.
  • 21
    • 85031140028 scopus 로고    scopus 로고
    • 13C NMR: δ 171.4, 137.3, 129.1, 128.5, 126.9, 73.3, 56.0, 52.7, 40.3
    • 13C NMR: δ 157.1, 156.1, 137.8, 129.4, 128.5, 126.5, 81.5, 70.4, 56.1, 54.4, 38.2, 28.1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.