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Volumn 2, Issue 14, 2004, Pages 2044-2049

Mimicking enzymatic transaminations: Attempts to understand and develop a catalytic asymmetric approach to chiral α-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; DENDRIMERS; ENZYMES; HIGH PRESSURE LIQUID CHROMATOGRAPHY; ISOMERIZATION;

EID: 3843108983     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404381b     Document Type: Article
Times cited : (42)

References (49)
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    • 85164466917 scopus 로고    scopus 로고
    • For catalytic asymmetric reactions in water see e.g.: Adv. Synth. Catal., 2002, 344, pp. 219-451.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 219-451
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    • 0004039284 scopus 로고
    • ed. P. D. Boyer, Academic Press, New York
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    • (1973) The Enzymes , vol.9
    • Braunstem, A.E.1
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    • 0004010351 scopus 로고
    • A. R. Liss, New York
    • 6 Catalysis, A. R. Liss, New York, 1984; (f) A. E. Martell, Acc. Chem. Res., 1989, 22, 115-124.
    • (1984) 6 Catalysis
    • Evangolopoulos, A.E.1
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    • 0000127613 scopus 로고
    • 6 Catalysis, A. R. Liss, New York, 1984; (f) A. E. Martell, Acc. Chem. Res., 1989, 22, 115-124.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 115-124
    • Martell, A.E.1
  • 8
    • 0004155427 scopus 로고    scopus 로고
    • W. E. Freeman and Company, New York
    • See e.g. L. Streyer, in Biochemistry, W. E. Freeman and Company, New York, 1999, p. 633.
    • (1999) Biochemistry , pp. 633
    • Streyer, L.1
  • 9
    • 0000225215 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 979-983
    • Metzler, D.E.1    Snell, E.E.2
  • 10
    • 3843085355 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 637
    • Ikawa, M.1    Snell, E.E.2
  • 11
    • 3843112540 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h)O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 644-648
    • Metzler, D.E.1    Olivard, J.2    Snell, E.E.3
  • 12
    • 0001454217 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 648-652
    • Metzler, D.E.1    Ikawa, M.2    Snell, E.E.3
  • 13
    • 33947455624 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 653-655
    • Ikawa, M.1    Snell, E.E.2
  • 14
    • 0343759328 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1956) Proc. Natl. Acad. Sci. USA , vol.42 , pp. 221-227
    • Longenecker, J.B.1    Snell, E.E.2
  • 15
    • 0001040376 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1331-1335
    • Matsushima, Y.1    Martell, A.M.2
  • 16
    • 0142044816 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5629-5631
    • Gansow, O.A.1    Holm, R.H.2
  • 17
    • 0343696709 scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 7211-7213
    • Matsumoto, S.1    Matsushima, Y.2
  • 18
    • 0037042284 scopus 로고    scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4978-4979
    • Liu, L.1    Brelow, R.2
  • 19
    • 0033135472 scopus 로고    scopus 로고
    • Selected papers: (a) D. E. Metzler and E. E. Snell, J. Am. Chem. Soc., 1952, 74, 979-983; (b) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 637; (c) D. E. Metzler, J. Olivard and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 644-648; (d) D. E. Metzler, M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 648-652; (e) M. Ikawa and E. E. Snell, J. Am. Chem. Soc., 1954, 76, 653-655; (f) J. B. Longenecker and E. E. Snell, Proc. Natl. Acad. Sci. USA, 1956, 42, 221-227; (g) Y. Matsushima and A. M. Martell, J. Am. Chem. Soc., 1967, 89, 1331-1335; (h) O. A. Gansow and R. H. Holm, J. Am. Chem. Soc., 1968, 90, 5629-5631; (i) S. Matsumoto and Y. Matsushima, J. Am. Chem. Soc., 1972, 94, 7211-7213; (j) L. Liu and R. Brelow, J. Am. Chem. Soc., 2002, 124, 4978-4979; (k) E. Fasella, S. D. Dong and R. Breslow, Bioorg. Med. Chem., 1999, 7, 709-714.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 709-714
    • Fasella, E.1    Dong, S.D.2    Breslow, R.3
  • 37
    • 3843066938 scopus 로고    scopus 로고
    • note
    • 2 as catalyst for the half-transamination of different α-keto esters 1 with pyridoxamine 2a or 4-picolylamine 2b did not yield any transamination product. See also reference 10.
  • 38
    • 0038102341 scopus 로고    scopus 로고
    • For P-N ligands in combination with Cu(I) see for instance: (a) Y. C. Hu, X. M. Liang, J. W. Wang, Z. Zheng and X. Q. Hu, J. Org. Chem., 2003, 68, 4542-4545; (b) L. Bernardi, A. S. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2003, 68, 2583-2591; (c) X. M. Fang, M. Johannsen, S. L. Yao, N. Gathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1999, 64, 4844-4849; (d) J. Andrien, B. R. Steele, C. G. Screttas, C. J. Cardin and J. Fornies, Organometallics, 1998, 17, 839-845.
    • (2003) J. Org. Chem. , vol.68 , pp. 4542-4545
    • Hu, Y.C.1    Liang, X.M.2    Wang, J.W.3    Zheng, Z.4    Hu, X.Q.5
  • 39
    • 0037419152 scopus 로고    scopus 로고
    • For P-N ligands in combination with Cu(I) see for instance: (a) Y. C. Hu, X. M. Liang, J. W. Wang, Z. Zheng and X. Q. Hu, J. Org. Chem., 2003, 68, 4542-4545; (b) L. Bernardi, A. S. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2003, 68, 2583-2591; (c) X. M. Fang, M. Johannsen, S. L. Yao, N. Gathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1999, 64, 4844-4849; (d) J. Andrien, B. R. Steele, C. G. Screttas, C. J. Cardin and J. Fornies, Organometallics, 1998, 17, 839-845.
    • (2003) J. Org. Chem. , vol.68 , pp. 2583-2591
    • Bernardi, L.1    Gothelf, A.S.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 40
    • 0033603563 scopus 로고    scopus 로고
    • For P-N ligands in combination with Cu(I) see for instance: (a) Y. C. Hu, X. M. Liang, J. W. Wang, Z. Zheng and X. Q. Hu, J. Org. Chem., 2003, 68, 4542-4545; (b) L. Bernardi, A. S. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2003, 68, 2583-2591; (c) X. M. Fang, M. Johannsen, S. L. Yao, N. Gathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1999, 64, 4844-4849; (d) J. Andrien, B. R. Steele, C. G. Screttas, C. J. Cardin and J. Fornies, Organometallics, 1998, 17, 839-845.
    • (1999) J. Org. Chem. , vol.64 , pp. 4844-4849
    • Fang, X.M.1    Johannsen, M.2    Yao, S.L.3    Gathergood, N.4    Hazell, R.G.5    Jørgensen, K.A.6
  • 41
    • 0003239360 scopus 로고    scopus 로고
    • For P-N ligands in combination with Cu(I) see for instance: (a) Y. C. Hu, X. M. Liang, J. W. Wang, Z. Zheng and X. Q. Hu, J. Org. Chem., 2003, 68, 4542-4545; (b) L. Bernardi, A. S. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 2003, 68, 2583-2591; (c) X. M. Fang, M. Johannsen, S. L. Yao, N. Gathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1999, 64, 4844-4849; (d) J. Andrien, B. R. Steele, C. G. Screttas, C. J. Cardin and J. Fornies, Organometallics, 1998, 17, 839-845.
    • (1998) Organometallics , vol.17 , pp. 839-845
    • Andrien, J.1    Steele, B.R.2    Screttas, C.G.3    Cardin, C.J.4    Fornies, J.5
  • 46
    • 3843115861 scopus 로고    scopus 로고
    • See reference 14b and literature cited therein
    • See reference 14b and literature cited therein.
  • 47
    • 3843107199 scopus 로고    scopus 로고
    • note
    • 2, then the solvent had to be removed under high vacuum before protecting the free amine, otherwise a part decomposition of the desired product occurs.


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