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Volumn 63, Issue 7, 1999, Pages 1304-1307

Novel synthesis of (−)-Bestatin from l-aspartic acid

Author keywords

Bestatin; Diastereoselective hydroxylation; L aspartic acid; hydroxy amino acid

Indexed keywords


EID: 0041782391     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.1304     Document Type: Article
Times cited : (7)

References (15)
  • 1
    • 0017236348 scopus 로고
    • Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes
    • Umezawa, H., Aoyagi, T., Suda, H., Hamada, M., and Takeuchi, T., Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes. J. Antibiot., 29, 97-101 (1976).
    • (1976) J. Antibiot. , vol.29 , pp. 97-101
    • Umezawa, H.1    Aoyagi, T.2    Suda, H.3    Hamada, M.4    Takeuchi, T.5
  • 2
    • 0017596420 scopus 로고
    • Synthesis and structure-activity relationships of bestatin analogues, inhibitors of aminopeptidase B
    • Nishizawa, R., Saino, T., Takita, T., Suda, H., Aoyagi, T., and Umezawa, H., Synthesis and structure-activity relationships of bestatin analogues, inhibitors of aminopeptidase B. J. Med. Chem., 20, 510-515 (1977)
    • (1977) J. Med. Chem. , vol.20 , pp. 510-515
    • Nishizawa, R.1    Saino, T.2    Takita, T.3    Suda, H.4    Aoyagi, T.5    Umezawa, H.6
  • 3
    • 0017131813 scopus 로고
    • Inhibition of aminopeptidase B and leucine aminopeptidase by bestatin and its stereoisomer
    • Suda, H., Aoyagi, T., Takeuchi, T., and Umezawa, H., Inhibition of aminopeptidase B and leucine aminopeptidase by bestatin and its stereoisomer. Arch. Biochem. Biophys., 177, 196-200 (1976)
    • (1976) Arch. Biochem. Biophys. , vol.177 , pp. 196-200
    • Suda, H.1    Aoyagi, T.2    Takeuchi, T.3    Umezawa, H.4
  • 4
    • 0020577840 scopus 로고
    • Identification and properties of the cell membrane bound leucine aminopeptidase interacting with the potential immunostimulant and chemotherapeutic agent bestatin
    • Leyhausen, G., Schuster, D. K., Vaith, P., Zahn, R. K., Umezawa, H., Falke, D., and Mueller, W. E. G., Identification and properties of the cell membrane bound leucine aminopeptidase interacting with the potential immunostimulant and chemotherapeutic agent bestatin. Biochem. Pharmacol., 32, 1051-1057 (1983).
    • (1983) Biochem. Pharmacol. , vol.32 , pp. 1051-1057
    • Leyhausen, G.1    Schuster, D.K.2    Vaith, P.3    Zahn, R.K.4    Umezawa, H.5    Falke, D.6    Mueller, W.E.G.7
  • 5
    • 0018815111 scopus 로고
    • Regio- and stereospecific synthesis of threo-3-amino-2-hydroxy-acids, novel amino acids containing aminopeptidase inhibitors of microbial origin
    • Kato, K., Sino, T., Nishizawa, R., Takita, T., and Umezawa, H., Regio- and stereospecific synthesis of threo-3-amino-2-hydroxy-acids, novel amino acids containing aminopeptidase inhibitors of microbial origin. J. Chem. Soc., Perkin Trans. I, 1618-1621 (1980)
    • (1980) J. Chem. Soc., Perkin Trans. I , pp. 1618-1621
    • Kato, K.1    Sino, T.2    Nishizawa, R.3    Takita, T.4    Umezawa, H.5
  • 6
    • 0020112101 scopus 로고
    • Stereo and regioselective openings of chiral 2,3-epoxy alcohols, versatile routes to optically pure natural products and drugs, unusual kinetic resolutions
    • Sharpless, K. B., Behrens, C. H., Katsuki, T., Lee, A. W. M., Martin, V. S., Takatani, M., Viti, S. M., Walker, F. J., and Woodard, S. S., Stereo and regioselective openings of chiral 2,3-epoxy alcohols, versatile routes to optically pure natural products and drugs, unusual kinetic resolutions. Pure Appl. Chem., 55, 589-604 (1983)
    • (1983) Pure Appl. Chem. , vol.55 , pp. 589-604
    • Sharpless, K.B.1    Behrens, C.H.2    Katsuki, T.3    Lee, A.W.M.4    Martin, V.S.5    Takatani, M.6    Viti, S.M.7    Walker, F.J.8    Woodard, S.S.9
  • 7
    • 0021181831 scopus 로고
    • A stereocontrolled synthesis of (—)-bestatin from an acyclic allylamine by iodocyclocarbamation
    • Kobayashi, S., Isobe, T., and Ohno, M., A stereocontrolled synthesis of (—)-bestatin from an acyclic allylamine by iodocyclocarbamation. Tetrahedron Lett., 25, 5079-5082 (1984);
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5079-5082
    • Kobayashi, S.1    Isobe, T.2    Ohno, M.3
  • 8
    • 0024450764 scopus 로고
    • Synthesis of β-Amino-α-hydroxy Acids via Aldol Condensation of a Chiral Glycolate Enolate. Synthesis of (—)-Bestatin
    • Pearson, W. H. and Hines, J. V., Synthesis of β-Amino-α-hydroxy Acids via Aldol Condensation of a Chiral Glycolate Enolate. Synthesis of (—)-Bestatin. J. Org. Chem., 54, 4235-4237 (1989)
    • (1989) J. Org. Chem. , vol.54 , pp. 4235-4237
    • Pearson, W.H.1    Hines, J.V.2
  • 9
    • 0025006910 scopus 로고
    • An improved one-pot method for stereoselective synthesis of the (2S',3R)-3-amino-2-hydroxy acids: Key intermediates for bestatin and amastatin
    • Herranz, R., Castro-Pichel, J., Vinuesa, S., and Garciα-Lopez, T., An improved one-pot method for stereoselective synthesis of the (2S',3R)-3-amino-2-hydroxy acids: key intermediates for bestatin and amastatin. J. Org. Chem., 55, 2232-2234 (1990)
    • (1990) J. Org. Chem. , vol.55 , pp. 2232-2234
    • Herranz, R.1    Castro-Pichel, J.2    Vinuesa, S.3    Garciα-Lopez, T.4
  • 10
    • 0026607899 scopus 로고
    • A stereocontrolled synthesis of the (2R,3S)- and (2S,3R)-3-amino-2-hydrox-ybutyric acid derivatives, the key components of a renin inhibitor and bestatin
    • Kobayashi, Y., Takemoto, Y., Kamijo, T., Harada, H., Ito, Y., and Terashima, S., A stereocontrolled synthesis of the (2R,3S)- and (2S,3R)-3-amino-2-hydrox-ybutyric acid derivatives, the key components of a renin inhibitor and bestatin. Tetrahedron, 48, 1853-1868 (1992)
    • (1992) Tetrahedron , vol.48 , pp. 1853-1868
    • Kobayashi, Y.1    Takemoto, Y.2    Kamijo, T.3    Harada, H.4    Ito, Y.5    Terashima, S.6
  • 11
    • 0026471808 scopus 로고
    • A stereospecific synthesis of (—)-bestatin from L-malic acid
    • Norman, B. H. and Morris, M. L., A stereospecific synthesis of (—)-bestatin from L-malic acid. Tetrahedron Lett., 33, 6803-6806 (1992)
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6803-6806
    • Norman, B.H.1    Morris, M.L.2
  • 12
    • 0027272436 scopus 로고
    • An enantio-divergent synthesis of threo-β-amino alcohols: Preparation of key intermediates for bestatin and the related peptides
    • Kawabata, T., Kiryu, Y., Sugiura, Y., and Fuji, K., An enantio-divergent synthesis of threo-β-amino alcohols: preparation of key intermediates for bestatin and the related peptides. Tetrahedron Lett., 34, 5127-5130 (1993).
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5127-5130
    • Kawabata, T.1    Kiryu, Y.2    Sugiura, Y.3    Fuji, K.4
  • 13
    • 0025799274 scopus 로고
    • Chemistry of aspartic acid and its application to drug-synthesis
    • Matsumoto, K. and Seki, M., Chemistry of aspartic acid and its application to drug-synthesis. J. Syn. Org. Chem. Jpn, (in Japanese), 49, 26-41 (1991)
    • (1991) J. Syn. Org. Chem. Jpn, (In Japanese) , vol.49 , pp. 26-41
    • Matsumoto, K.1    Seki, M.2
  • 14
    • 0008481013 scopus 로고
    • Chemistry of amino acids and its application to drug synthesis
    • Seki, M. and Matsumoto, K., Chemistry of amino acids and its application to drug synthesis. Bioindustry, (in Japanese), 1995, 5-19 (1995).
    • (1995) Bioindustry, (In Japanese) , vol.1995 , pp. 5-19
    • Seki, M.1    Matsumoto, K.2
  • 15
    • 85009552278 scopus 로고    scopus 로고
    • A novel synthesis of allophenylnor-statine from (I?)-aspartic acid
    • (in press)
    • Seki, M. and Matsumoto, K., A novel synthesis of allophenylnor-statine from (i?)-aspartic acid. Synthesis (in press).
    • Synthesis
    • Seki, M.1    Matsumoto, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.