Designing enzymatic resolution of amines

Abstract

A new strategy, utilizing IR and mass spectrometry, has been developed to design appropriate reagents and reaction conditions for enantioselective enzymatic protection of amines with readily removable protecting groups.

References

1. A. M. Klibanov, Acc. Chem. Res., 1990, 23, 114.
2. Y.-F. Wang, J. J. Lalonde, M. Momongan, D. E. Bergbreiter and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 7200; H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 1986, 108, 6421; J. M. Fang and C.-H. Wong, Synlett, 1994, 6, 393; M. Degueil-Castaing, B. DeJeso, S. Drouillard and B. Maillard, Tetrahedron Lett., 1987, 28, 953; J. B. West, J. Scholten, N. J. Stolowich, J. L. Hogg, A. I. Scott and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 3709; A. Ghogare and G. S. Kumar, J. Chem. Soc., Chem. Commun., 1989, 1533; V. Gotor and R. Pulido, J. Chem. Soc., Perkin Trans. 1, 1991, 491; M. Pozo, R. Puliddo and V. Gortor, Tetrahedron, 1992, 48, 6477; G. Kretzsdchmar and M. Schudok, Tetrahedron Lett., 1997, 38, 387.
3. A. Zaks and D. R. Dodds, Drug Discovery Today, 1997, 2, 513; K. Faber, Biotransformations in Organic Chemistry, Springer, Heidelberg, 1995; C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
4. (a) F. Balkenhohl, K. Ditrich, B. Hauer and W. Ladner, J. Prakt. Chem., 1997, 339, 381; (b) V. Gotor, E. Menendez, Z. Mouloungui and A. Gasset, J. Chem. Soc., Chem. Commun., 1993, 2453; (c) V. Gotor, Tetrahedron, 1993, 49, 4321; (d) H. Kitaguchi, P. A. Fitspatrick, J. E. Huber and A. M. Klibanov, J. Am. Chem. Soc., 1989, 111, 3094; (e) B. Orsat, P. B. Alper, W. J. Moree, C.-P. Mak and C.-H. Wong, J. Am. Chem. Soc., 1996, 118, 712; (f) M. Pozo and V. Gotor, Tetrahedron, 1993, 49, 10725; (g) M. Pozo and V. Gotor, Tetrahedron, 1993, 49, 4321; (h) S. Puertas, F. Robelledo and V. Gotor, Tetrahedron, 1995, 51, 1495; (i) S. Takayama, W. J. Moree and C.-H. Wong, Tetrahedron Lett., 1996, 35, 6287; (j) A. L. Gutman, E. Meyer, E. Kalerin, F. Polyak and J. Sterling, Biotechnol. Bioeng., 1992, 40, 760; (k) K.-E. Jaeger, K. Liebeton, A. Zonta, K. Schimossek and M. T. Reetz, Appl. Microbiol. Biotechnol., 1996, 46, 99; (l) S. Fernandez, R. Brieva, F. Rebolledo and V. Gotor, J. Chem. Soc., Chem. Commun., 1992, 2885; (m) E. Schoffers, A. Golebiowski and C. R. Johnson, Tetrahedron, 1996, 52, 3769; (n) M. Pozo, R. Pulido and V. Gotor, Tetrahedron, 1992, 48, 6477.
5. For n values see: R. M. Silverstein, G. C. Bassler and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York, 1991.
6. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; R. Madsen, C. Roberts and B. Fraser-Reid, J. Org. Chem., 1995, 60, 7920.
7. A. Maestro, C. Astorga and V. Gotor, Tetrahedron: Asymmetry, 1997, 8, 3153.
8. S. Takayama, R. Martin, J. Wu, K. Laslo, G. Siuzdak and C.-H. Wong, J. Am. Chem. Soc., 1997, 119, 8146; J. Wu, S. Takayama, C.-H. Wong and G. Siuzdak, Chem. Biol., 1997, 4, 653.