Stereoselective enzymatic hydrolysis of dimethyl meso-piperidine-3,5-dicarboxylates

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 345-348

  Danieli, Bruno ^a   Lesma, Giordano ^a   Passarella, Daniele ^a   Silvani, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 PIPERIDINEDICARBOXYLIC ACID DIMETHYL ESTER; ESTER; ESTERASE; PIPERIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; ENANTIOMER; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIVER; MUCOR; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PANCREAS; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS; REACTION ANALYSIS; SWINE;

EID: 0030063282     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00002-X     Document Type: Article

References (13)

1. Part of this work was presented at the Eight European Symposium on Organic Chemistry, Sitges, Barcelona, Spain, August 1993.
2. Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. J. Org. Chem. 1995, 60, 2506-2513 and references cited therein.
3. Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso-Compounds, in Advances in the Use of Synthons in Organic Chemistry; Dondoni, A.; Ed.; 1993; Vol. 1, pp. 143-219.
4. +, 51), 200(100).
5. Stetter, H.; Hennig, H. Chem. Ber. 1955, 88, 789-795.
6. In these conditions 2a (3S, 5R) showed at 5 3.69 for the methyl group of the methoxycarbonyl while, ent-2a (3R, 5S) showed at 8 3.67.
7. +, 66), 186(100).
8. Barton, D.H.R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1988, 44, 5479-5486
9. Wirz, B.; Walther, W. Tetrahedron: Asym. 1992, 3, 1049-1054.
10. GC separation of the enantiomers of 4 was performed on permethylated 50 m β-cyclodextrine (CD-M) column (150-200°C with 1°C/min).
11. Wong, C.H.; Whitesides, G.M. Enzymes in Synthetic Organic Chemistry, in Tetrahedron Organic Chemistry Series; Baldwin, J.E.; Magnus, P.D.; Eds.; Pergamon, 1994, Vol. 12, pp. 94-98.
12. All calculations were performed with HyperChem program (release 4.0, Autodesk, Inc.). Candidate conformations were generated by dihedral driving using constrained minimization. Once the alternative conformation was generated, constraints were removed and the structure was reminimized.
13. These results were consistent with a recent report on molecular mechanics study of acylpiperidine conformations, see: Schnur, D.M.; Yuh, Y.H.; Dalton, D.R. J. Org. Chem. 1989, 54, 3779-3785. In addition these calculations showed that for 2a the chair conformations with the two methoxycarbonyl groups equatorial disposed, are more stable by about 0.40-0.58 Kcal/mol with respect to the others with the same groups axially oriented. In the case of compound 2c, this difference ranges from 0.46 to 0.65 Kcal/mol in the opposite sense.