Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 6001-6004

  Maddrell, Samuel J ^a   Turner, Nicholas J ^a,c   Kerridge, Alison ^a   Willetts, Andrew J ^a   Crosby, John ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; HYDROLYASE; MEVINIC ACID DERIVATIVE; NITRILE;

ARTICLE; CATALYSIS; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581374     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01259-2     Document Type: Article

References (20)

1. 2. See H. Yamada in Biocatalysis, Large Scale Conversion of Nitriles into Useful Amides and Acids, Ed. D.A. Abramovicz, Van Nostrand Reinhold, New York, 1990, p.227. For a recent review of the synthetic applications of nitrile hydrolases see; Crosby, J.; Moilliet, J.; Parratt, J.S.; Turner, N.J.; J. Chem. Soc., Perkin Trans. 1, 1994, 1679.
2. 2. See H. Yamada in Biocatalysis, Large Scale Conversion of Nitriles into Useful Amides and Acids, Ed. D.A. Abramovicz, Van Nostrand Reinhold, New York, 1990, p.227. For a recent review of the synthetic applications of nitrile hydrolases see; Crosby, J.; Moilliet, J.; Parratt, J.S.; Turner, N.J.; J. Chem. Soc., Perkin Trans. 1, 1994, 1679.
3. 3. Cohen, M. A.; Sawden, J.; Turner, N. J.; Tetrahedron Lett., 1990, 31, 7223; de Raadt, A.; Klempier, N.; Faber, K.; Griengl, H.; J. Chem. Soc., Perkin Trans. 1, 1992, 137; Thompson, L. A.; Knowles, C. J.; Linton, E. A.; Wyatt, J. M.; Chem. Brit., 1988, 24, 900; Fukada, Y.; Harada, T.; Izumi, Y.; J. Ferment. Technol., 1973, 51, 393.
4. 3. Cohen, M. A.; Sawden, J.; Turner, N. J.; Tetrahedron Lett., 1990, 31, 7223; de Raadt, A.; Klempier, N.; Faber, K.; Griengl, H.; J. Chem. Soc., Perkin Trans. 1, 1992, 137; Thompson, L. A.; Knowles, C. J.; Linton, E. A.; Wyatt, J. M.; Chem. Brit., 1988, 24, 900; Fukada, Y.; Harada, T.; Izumi, Y.; J. Ferment. Technol., 1973, 51, 393.
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13. 2O, 45%; b) NaH, BnBr, THF, 41%.
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15. 10. The lower e.e. of (S)-5 from the large scale run is believed to be a consequence of the longer reaction time (24h) compared to small scale experiments (6h). There is some evidence that Brevibacterium R312 may contain a racemase that has activity towards 5. Prolonged exposure to the racemase would account for the reduction in optical purity. Experiments are underway to verify this observation.
16. 11. Bennett, F.; Knight, D. W.; Fenton, G.; J. Chem. Soc., Perkin Trans. 1, 1991, 133.
17. 12. The requirement for the presence of catalytic quantities of 2,2,2-trichloroacetamide was discovered during hydrogenation of racemic samples of 5 which were contaminated with trace amounts of the amide and were found to give reproducibly higher yields of the alcohol 6. It is possible that partial reduction of the nitrile occurs to give the amine which may poison the catalyst and that addition of 2,2,2-trichloroacetamide inhibits this process.
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