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Volumn 52, Issue 37, 1996, Pages 12125-12136

α-Alkylation of α-amino esters by using a pyridoxal model compound having a Li+-ionophore character

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDOXAL;

EID: 0030576847     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00704-1     Document Type: Article
Times cited : (10)

References (23)
  • 2
    • 0021251618 scopus 로고
    • 2. For example: Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. J. Med. Chem., 1984, 27, 713-717; Saari, W. S.; Freedman, M. B.; Hartman, R. D.; King, S. W.; Raab, A. W.; Randall, W. C.; Engelhardt, E. L.; Hirschmann, R.; Rosegay, A.; Ludden, C. T.; Scriabine, A. J. Med. Chem., 1978, 21, 746-753; Ramalingam, K.; Woodard, R. W. Tetrahedron Lett., 1985, 26, 1135-1136; Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc., 1980, 102, 7136-7138.
    • (1984) J. Med. Chem. , vol.27 , pp. 713-717
    • Saari, W.S.1    Halczenko, W.2    Cochran, D.W.3    Dobrinska, M.R.4    Vincek, W.C.5    Titus, D.G.6    Gaul, S.L.7    Sweet, C.S.8
  • 4
    • 0021967283 scopus 로고
    • 2. For example: Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. J. Med. Chem., 1984, 27, 713-717; Saari, W. S.; Freedman, M. B.; Hartman, R. D.; King, S. W.; Raab, A. W.; Randall, W. C.; Engelhardt, E. L.; Hirschmann, R.; Rosegay, A.; Ludden, C. T.; Scriabine, A. J. Med. Chem., 1978, 21, 746-753; Ramalingam, K.; Woodard, R. W. Tetrahedron Lett., 1985, 26, 1135-1136; Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc., 1980, 102, 7136-7138.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1135-1136
    • Ramalingam, K.1    Woodard, R.W.2
  • 5
    • 0000003184 scopus 로고
    • 2. For example: Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. J. Med. Chem., 1984, 27, 713-717; Saari, W. S.; Freedman, M. B.; Hartman, R. D.; King, S. W.; Raab, A. W.; Randall, W. C.; Engelhardt, E. L.; Hirschmann, R.; Rosegay, A.; Ludden, C. T.; Scriabine, A. J. Med. Chem., 1978, 21, 746-753; Ramalingam, K.; Woodard, R. W. Tetrahedron Lett., 1985, 26, 1135-1136; Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc., 1980, 102, 7136-7138.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7136-7138
    • Walsh, J.J.1    Metzler, D.E.2    Powell, D.3    Jacobson, R.A.4
  • 6
    • 0019418763 scopus 로고
    • 3. For example: Shoji, J.; Ninoo, H.; Kato, T.; Nakauchi, K.; Matsuura, S.; Mayama, M.; Yasuda, Y.; Kawamura, Y. J. Antibiotics, 1981, 34, 374-380; Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiotics, 1981, 34, 1615-1618; Fukushima, K.; Arai, T.; Mori, Y.; Tsuboi, M.; Suzuki, M. J. Antibiotics, 1983, 36, 1613-1630; Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett., 1985, 26, 1073-1076.
    • (1981) J. Antibiotics , vol.34 , pp. 374-380
    • Shoji, J.1    Ninoo, H.2    Kato, T.3    Nakauchi, K.4    Matsuura, S.5    Mayama, M.6    Yasuda, Y.7    Kawamura, Y.8
  • 7
    • 0019772514 scopus 로고
    • 3. For example: Shoji, J.; Ninoo, H.; Kato, T.; Nakauchi, K.; Matsuura, S.; Mayama, M.; Yasuda, Y.; Kawamura, Y. J. Antibiotics, 1981, 34, 374-380; Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiotics, 1981, 34, 1615-1618; Fukushima, K.; Arai, T.; Mori, Y.; Tsuboi, M.; Suzuki, M. J. Antibiotics, 1983, 36, 1613-1630; Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett., 1985, 26, 1073-1076.
    • (1981) J. Antibiotics , vol.34 , pp. 1615-1618
    • Morimoto, K.1    Shimada, N.2    Naganawa, H.3    Takita, T.4    Umezawa, H.5
  • 8
    • 0021059178 scopus 로고
    • 3. For example: Shoji, J.; Ninoo, H.; Kato, T.; Nakauchi, K.; Matsuura, S.; Mayama, M.; Yasuda, Y.; Kawamura, Y. J. Antibiotics, 1981, 34, 374-380; Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiotics, 1981, 34, 1615-1618; Fukushima, K.; Arai, T.; Mori, Y.; Tsuboi, M.; Suzuki, M. J. Antibiotics, 1983, 36, 1613-1630; Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett., 1985, 26, 1073-1076.
    • (1983) J. Antibiotics , vol.36 , pp. 1613-1630
    • Fukushima, K.1    Arai, T.2    Mori, Y.3    Tsuboi, M.4    Suzuki, M.5
  • 9
    • 0021917543 scopus 로고
    • 3. For example: Shoji, J.; Ninoo, H.; Kato, T.; Nakauchi, K.; Matsuura, S.; Mayama, M.; Yasuda, Y.; Kawamura, Y. J. Antibiotics, 1981, 34, 374-380; Morimoto, K.; Shimada, N.; Naganawa, H.; Takita, T.; Umezawa, H. J. Antibiotics, 1981, 34, 1615-1618; Fukushima, K.; Arai, T.; Mori, Y.; Tsuboi, M.; Suzuki, M. J. Antibiotics, 1983, 36, 1613-1630; Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett., 1985, 26, 1073-1076.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1073-1076
    • Mori, T.1    Takahashi, K.2    Kashiwabara, M.3    Uemura, D.4    Katayama, C.5    Iwadare, S.6    Shizuri, Y.7    Mitomo, R.8    Nakano, F.9    Matsuzaki, A.10
  • 11
    • 0028300898 scopus 로고
    • 5. For recent review for asymmetric synthesis of α-amino acids by α-alkylation: O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron, 1994, 50, 4507-4518.
    • (1994) Tetrahedron , vol.50 , pp. 4507-4518
    • O'Donnell, M.J.1    Wu, S.2    Huffman, J.C.3
  • 13
    • 85030270387 scopus 로고    scopus 로고
    • For instance, it is known that 3-O-methylpyridoxal does not exhibit non-enzymatic transamination: see ref. 9
    • 7. For instance, it is known that 3-O-methylpyridoxal does not exhibit non-enzymatic transamination: see ref. 9.
  • 18
    • 33947455624 scopus 로고
    • We selected a pyridine ring as a basic skeleton by taking into account of the chelation ability of the nitro group with hard metal ions
    • 12. Pyridoxal model having a nitrobenzene-ring instead of a pyridine-ring was reported to show non-enzymatic transamination activity [Ikawa, M.; Snell, E. E. J. Am. Chem. Soc., 1954, 76, 653-655]. We selected a pyridine ring as a basic skeleton by taking into account of the chelation ability of the nitro group with hard metal ions.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 653-655
    • Ikawa, M.1    Snell, E.E.2
  • 20
    • 49549144715 scopus 로고
    • 14. Roth, K.; Grosse, M.; Rewicki, D. Tetrahedron Lett., 1972, 435-438; Otera, J.; Shiomi, T.; Murakami, K.; Kawasaki, Y. Bull. Chem. Soc. Jpn., 1981, 54, 2964-2967; Otera, J.; Yano, T.; Kusakabe, K. ibid., 1983, 56, 1057-1059.
    • (1972) Tetrahedron Lett. , pp. 435-438
    • Roth, K.1    Grosse, M.2    Rewicki, D.3
  • 21
    • 0011779234 scopus 로고
    • 14. Roth, K.; Grosse, M.; Rewicki, D. Tetrahedron Lett., 1972, 435-438; Otera, J.; Shiomi, T.; Murakami, K.; Kawasaki, Y. Bull. Chem. Soc. Jpn., 1981, 54, 2964-2967; Otera, J.; Yano, T.; Kusakabe, K. ibid., 1983, 56, 1057-1059.
    • (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 2964-2967
    • Otera, J.1    Shiomi, T.2    Murakami, K.3    Kawasaki, Y.4
  • 22
    • 0011787118 scopus 로고
    • 14. Roth, K.; Grosse, M.; Rewicki, D. Tetrahedron Lett., 1972, 435-438; Otera, J.; Shiomi, T.; Murakami, K.; Kawasaki, Y. Bull. Chem. Soc. Jpn., 1981, 54, 2964-2967; Otera, J.; Yano, T.; Kusakabe, K. ibid., 1983, 56, 1057-1059.
    • (1983) Bull. Chem. Soc. Jpn. , vol.56 , pp. 1057-1059
    • Otera, J.1    Yano, T.2    Kusakabe, K.3


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