Lipase Mediated Resolution of γ-Branched Chain Fatty Acid Methyl Esters

References

• Barbieri G., Bolzoni L., Parolari G., Virgili R., Buttini R., Careri M., et al. Flavor compounds of dry-cured ham. J. Agric. Food. Chem 1992; 40: 2389–2394
   Web of Science ®Google Scholar
• Besler B., Mertz K., Kollman P. Atomic charges derived from semi-empirical methods. J. Comp. Chem 1990; 11: 431–439
   Web of Science ®Google Scholar
• Boelens M. H., Boelens H., van Gemert L. J. Sensory properties of optical isomers. Perfumer and Flavorist 1993; 18: 1–16
   Google Scholar
• Bovara R., Carrea G., Ottolina G., Riva S. Effects of water activity on Vmax and Km of lipase catalyzed transesterification in organic media. Biotechnol. Lett 1993; 15: 937–942
   Web of Science ®Google Scholar
• Brennand C. P., Lindsay R. C. Distribution of volatile branched-chain fatty acids in various lamb tissues. Meat Sci 1992; 31: 411–421
   PubMedGoogle Scholar
• Brennand C. P., Lindsay R. C. Influence of cooking on concentrations of species-related flavor compounds in mutton. Food Sci. Technol 1993; 25: 357–364
   Google Scholar
• Bühler M., Wandrey Ch. Enzymatische Fettspaltung. Fett Wissenschaft Technologie 1987; 89: 156–164
   Google Scholar
• Cambou B., Klibanov A. M. Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: asymmetric hydrolysis, esterification and transesterification. Biotechnol. Bioeng 1984; 26: 1449–1454
   PubMed Web of Science ®Google Scholar
• Carrea G., Ottolina G., Riva S., Secundo F. Effect of reaction conditions on the activity and enantioselectivity of lipases in organic solvents. In Biocatalysis in Non-Conventional Media, J. Tramper, et al. Elsevier, Amsterdam 1992; 111–119
   Google Scholar
• Chen C.-S., Fujimoto Y., Girdaukas G., Sih C. J. Quantitative analysis of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc 1982; 104: 7294–7299
   Web of Science ®Google Scholar
• Chen C.-S., Wu S.-H., Girdaukas G., Sih C. J. Quantitative analysis of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems. J. Am. Chem. Soc 1987; 109: 2812–2817
   Web of Science ®Google Scholar
• Chuman T., Noguchi M. The aroma constituents of Turkish tobacco. Part III. Acidic aroma components of turkish tobacco. Agric. Biol. Chem 1977; 41: 1021–1030
   Web of Science ®Google Scholar
• Elferink V. H.M., Breitgoff D., Kloosterman M., Kamphuis J., van den Tweel W. J.J., Meijer E. M. Industrial developments in biocatalysis. Reel. Trav. Chim. Pays-Bas 1991; 110: 63–74
   Google Scholar
• Engel K.-H. Lipase-catalyzed enantioselective acidolysis of chiral 2-methylalkanoates. JAOCS 1992; 69: 146–150
   Google Scholar
• Faber K., Franssen M. C.R. Prospects for the increased application of biocatalysts in organic transformations. TIBTECH 1993; 11: 461–470
   PubMedGoogle Scholar
• Ha J. K., Lindsay R. C. Volatile branched-chain fatty acids and phenolic compounds in aged Italian cheese flavors. J. Food Sci 1991; 56: 1241–1250
   Web of Science ®Google Scholar
• Hallet R. H., Perez A. L., Gries G., Gries R., Pierce H. D., Jr., Yue J., et al. Aggregation pheromone of coconut rhinoceros beetle, Oryctes rhinoceros (L.) (Coleoptera: Scarabaeidae). J. Chem. Ecol 1995; 21: 1549–1570
   PubMedGoogle Scholar
• Holmberg E., Szmulik P., Norin T., Hult K. Hydrolysis and esterificalion with lipase from Candida cylindraeea Influence of the reaction conditions and acid moiety on the enantiomeric excess. Biocatalysis 1989; 2: 217–223
   Google Scholar
• Jensen R. G., Galluzzo D. R., Bush V. J. Selectivity is an important characteristic of lipases (acylglycerol hydrolases). Biocatalysis 1990; 3: 307–316
   Google Scholar
• John V. T., Abraham G. Lipase catalysis and its applications. Biocatalysis for Industry, J. S. Dordick. Plenum, New York 1991; 193
   Google Scholar
• Karl V., Kaunzinger A., Gutser J., Steuer P., Angles-Angel J., Mosandl A. Stereoisomeric flavour compounds LXVII. 2-. 3-. and 4-alkyl-branched acids, part 1: General approach to the synthesis of the enantiopure acids. Chiralily 1994; 6: 420–426
   Google Scholar
• Kelly S. M., Buchecker R. Ferroelectric liquid crystals. Chiral phenyl benzoates incorporating a trans-1,4-disubstituted cyclohexane ring. Helv. Chim. Acta 1988; 71: 451–460
   Web of Science ®Google Scholar
• Klibanov A. M. Asymmetric transformations catalyzed by enzymes in organic solvents. Ace. Chem. Res 1990; 23: 114–120
   Web of Science ®Google Scholar
• Kloosterman M., Elferink V. H.M., van lersel J., Roskam J.-H., Meijer E. M., Hulshof L. A., Sheldon R. A. Lipases in the preparation of β-blockers. TIBTECH 1988; 6: 251–256
   Web of Science ®Google Scholar
• Krapcho A. P. Synthetic applications of dealkoxycarbonylations of malonate esters, β-keto esters, α-cyano esters and related compounds in dipolar aprotic media — part 1. Synthesis 1982; 805–822
   Google Scholar
• Macrae A. R. Lipase-catalyzed interesterification of oils and fats. JAOCS 1983; 60: 291–294
   Web of Science ®Google Scholar
• Matsuzaki T., Shinozaki Y., Hagimori M., Tobita T., Shigemalsu H., Koiwai A. Novel glycerolipids and glycolipids from the surface lipids of Nieotiana benthaniana. Biosci. Biotechnol. Biochem 1992; 56: 1565–1569
   PubMed Web of Science ®Google Scholar
• Matsuzaki T., Shinozaki Y., Suhara S. Isolation of sucrose fatty acid esters from wild tobacco. 1993; 489–494, J.P, 05. 186. Chan. Abstr., 119(1993). 199844g
   Google Scholar
• Mukherjee K. D. Lipase-catalyzed reactions for modification of fats and other lipids. Biocatalysis 1990; 3: 277–293
   Google Scholar
• Norin M., Mattson A., Hult K., Norin T. Molecular modelling of chymotrypsin-substrate interactions: Calculation of enantioselectivity. Biocatalysis 1993; 7: 131–147
   Google Scholar
• Padt A., van der Sewalt J. J.W., Agoston S. M.I., Van't Riet K. Candida rugosa lipase stability during acylglycerol synthesis. Enzyme Microb. Technol 1992; 14: 805–812
   Google Scholar
• Seino H., Uchibori T., Nishitani T., Inamasu S. Enzymatic synthesis of carbohydrate esters of fatty acid (1) esterification of sucrose, glucose, fructose and sorbitol. JAOCS 1984; 61: 1761–1765
   Web of Science ®Google Scholar
• Simpson R. F., Miller G. C. Aroma composition of Chardonnay wine. Vitis 1984; 23: 143–158
   Google Scholar
• Sonnet P. E., Welch Baillargeon M. Kinetic resolution of secondary alcohols with commercial lipases: application to rootworm sex pheromone synthesis. J. Chem. Ecol 1987; 13: 1279–1292
   PubMedGoogle Scholar
• Sreenivasan B. Interesterification of fats. JAOCS 1978; 55: 796–805
   Web of Science ®Google Scholar
• Tanner D. D., Osman S. A.A. Oxidative decarboxylation. On the mechanism of the potassium persulfate promoted decarboxylation reaction. J. Org. Chem 1987; 52: 4689–4693
   Web of Science ®Google Scholar
• Uppenberg J., Trier Hansen M., Patkar S., Jones A. The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica. Structure 1994; 2: 293–308
   PubMed Web of Science ®Google Scholar
• Uppenberg J., Öhrner N., Norin M., Hult M., Kleywegl G. J., Patkar S., et al. Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry 1995; 34: 16838–16851
   PubMed Web of Science ®Google Scholar
• Valivety R. H., Hailing P. J., Macrae A. R. Water as a competitive inhibitor of lipase-catalysed esterification in organic media. Biotechnol. Lett 1993; 15: 1133–1138
   Web of Science ®Google Scholar
• Wilson W. K., Baca S. B., Barber Y. L., Scallen T. J., Morrow C. J. Enanlioselective hydrolysis of 3-hydroxy-3-methylalkanoic acid esters with pig liver esterase. J. Org. Chem 1983; 48: 3960–3966
   Google Scholar
• Zaks A., Klibanov A. M. Enzyme-catalyzed processes in organic solvents. Proc. Sail. Acad. Sci. USA 1985; 82: 3192–3196
   PubMed Web of Science ®Google Scholar