Lipase-catalysed enantioselective hydrolysis: Interpretation of the kinetic results in terms of frontier orbital localisation

Tetrahedron

Volumn 53, Issue 13, 1997, Pages 4889-4900

  Parve, Omar ^a   Vallikivi, Imre ^a   Metsala, Andrus ^a   Lille, Ülo ^a   Tõugu, Vello ^b   Sikk, Peeter ^b   Käämbre, Tuuli ^b   Vija, Heiki ^b   Pehk, Tõnis ^b  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; BICYCLO[3.2.0]HEPTANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030889256     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00184-1     Document Type: Article

References (30)

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19. Examination of molecular framework models proved that the linearly remote substituents present in a bicyclic molecule can be located rather close to each other in space (for instance, the ester groups of S10).
20. The initial velocities were calculated from the slope of NaOH consumption vs. time plot during 5-25% conversion.
21. 21,23) to correspond to those presented in the tables.
22. 6).
23. The optical rotation value corresponds to the hydrolytically less active enantiomer separated from the hydrolysis product over silica and being estimated to the pure enantiomer by NMR using chiral shift reagent.
24. Parve, O.; Vallikivi, I.; Lahe, L.; Metsala, A.; Lille, Ü.; Tõugu, V.; Vija, H.; Pehk, T. Lipase-Catalysed Enantioselective Hydrolysis of Bicyclo[3.2,0]heptanol Esters in Supercritical Carbon Dioxide. Bioorg. Medicinal Chem. Lett. (in press).
25. Lipolase 100L (Preparation of Humicola lanuginosa lipase - HLL; Novo Industri A/S, Denmark); declared activity: 100 KLU/G; batch No. LAN 0002 90-6).
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27. 19 was estimated to affect the initial rate not more than 10%. It should be emphasized that the differences in initial rates discussed are mainly in the range of one order of magnitude or more.
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29. Dewar, M.J.S.; Thiel, W. J. Am. Chem. Soc., 1977, 99, 4899.
30. max [μmol/min] 9.1 32.4 56.2 41.7 70.8 64.6 60.3