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Volumn , Issue 7, 2000, Pages 1046-1048

Facile synthesis of 3,4-dihydroxyprolines as an application of the L- threonine aldolase-catalyzed aldol reaction

Author keywords

hydroxy L amino acids; 3,4 dihydroxyproline; Aldol reactions; Enzymes; L threonine aldolase

Indexed keywords

3,4 DIHYDROXYPROLINE; FRUCTOSE BISPHOSPHATE ALDOLASE;

EID: 0033931576     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (34)

References (29)
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    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
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    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
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    • (1985) Tetrahedron Lett. , vol.26 , pp. 5307
    • Ohfune, Y.1    Kurokawa, N.2
  • 13
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    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
    • (1981) Liebigs Ann. Chem. , pp. 1445
    • Karl, J.-U.1    Wieland, T.2
  • 14
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    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
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    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
    • (1992) J. Chem. Soc. Perkin. Trans I , vol.1 , pp. 1901
    • Moss, W.O.1    Bradbury, R.H.2    Hales, N.J.3    Gallagher, T.4
  • 16
    • 0003074567 scopus 로고
    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 51
    • Moss, W.O.1    Bradbury, R.H.2    Hales, N.J.3    Gallagher, T.4
  • 17
    • 0000848997 scopus 로고
    • Synthesis of I: Bols, M.; Lundr, I. Acta Chem. Scand. 1992, 46, 298. Kim, J. H.; Lee, W. S.; Tang, M. S.; Lee, S. G.; Park, K. H. Synlett 1999, 614. Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Karl, J.-U.; Wieland, T. Liebigs Ann. Chem. 1981, 1445. Synthesis of 2: Defoin, A.; Sifferlen, T.; Streith, J. Synlett 1997, 1294. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc. Perkin. Trans I 1992, 1901. Moss, W. O.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1990, 51. Austin, G. N.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
    • (1987) Tetrahedron , vol.43 , pp. 3095
    • Austin, G.N.1    Baird, P.D.2    Fleet, G.W.J.3    Peach, J.M.4    Smith, P.W.5    Watkin, D.J.6
  • 23
    • 0343189459 scopus 로고    scopus 로고
    • note
    • Compound 6 was completely consumed in the reaction with L-AAO (12 μM substrate in 1 mL of Tris buffer (10 mM, pH 8.5), 5 U of the enzyme, 30 °C, 3 days) but was not changed by D-AAO under the same conditions.
  • 24
    • 0343189458 scopus 로고    scopus 로고
    • note
    • +): 345.1553. Found: 354.1505.
  • 25
    • 0343625019 scopus 로고    scopus 로고
    • note
    • +): 345.1553. Found: 354.1566.
  • 27
    • 0343189454 scopus 로고    scopus 로고
    • note
    • Bols et al. have synthesized compound 1 from the analogous intermediate of lactone 10. 6
  • 28
    • 0343189455 scopus 로고    scopus 로고
    • note
    • 4 MW, 147).


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