Influence of ester chain length, enzyme, and physical parameters on lipase-catalysed hydrolyses of meso-oxiranedimethanol esters. Part 2

Tetrahedron Asymmetry

Volumn 11, Issue 15, 2000, Pages 3197-3209

  Moseley, Jonathan D ^a,b   Staunton, James ^b  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHYLENE OXIDE DERIVATIVE; METHANOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; HYDROLYSIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034637350     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00276-7     Document Type: Article

References (19)

1. Moseley, J. D.; Staunton, J. Tetrahedron: Asymmetry 1998, 9, 3619-3623.
2. Schloss, J. V.; Hartman, F. C. Bioorg. Chem. 1980, 9, 217-226.
3. Nelson, W. L.; Freeman, D. S.; Vincenzi, F. F. J. Med. Chem. 1976, 19, 153-158.
4. Aside from poor performance in the esterification step, the inferior quality was typified by its less crystalline appearance and lower melting point (47-49°C in our hands by Nelson's method against 50-52°C using Schloss' method; Nelson reported 44-47°C). This may be accounted for by the fact that the material was isolated from water by freeze drying, probably resulting in an amorphous or less crystalline form, and possibly retained water.
5. All enzymes are commercially available from Fluka (F) except CCL and PLE available from Sigma (S), and PPL from both. Abbreviations used: CCL, lipase from Candida cylindracea; LAN, lipase from Aspergillus niger; LCL, lipase from Candida lipolytica; LMJ, lipase from Mucor javanicus; LPF, lipase from Pseudomonas fluorescens; LPR, lipase from Penicillium roqueforti; LRA, lipase from Rhizopus arrhizus; LRD, lipase from Rhizopus delemar; LRN, lipase from Rhizopus niveus; PLE, pig liver esterase; PPL porcine pancreatic lipase.
6. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1991, 32, 3043-3046.
7. Brevet, J.-L.; Mori, K. Synthesis 1992, 1007-1012.
8. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
9. Corser, D. A.; Dart, R. K.; Marples, B. A. J. Chem. Res. (S) 1992, 66-67.
10. The Sigma derived PPL was moderately inferior, perhaps due to the source or method of isolation.
11. Joerger, R. D.; Haas, M. J. Lipids 1994, 29, 377.
12. 6 although they mirrored their results in all other respects. We offer three possibilities for the observed differences; (i) differences in enzyme source (Fluka versus Sigma); (ii) differences in the w/w quantity of enzyme used; and (iii) our preparations were run to 100% conversion, theirs to a maximum of 90%.
13. Kvittingen, L.; Sjursnes, B.; Halling, P.; Anthonsen, T. Tetrahedron 1992, 48, 5259-5264.
14. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
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17. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1992, 33, 5355-5358.
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19. Trincone, A.; Pagnotta, E. Tetrahedron: Asymmetry 1996, 7, 2773-2774.