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Original Articles

Regioselective Hydrolysis of Carbohydrate Secondary Acyl Esters By Lipases1

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Pages 333-341 | Received 12 Apr 1988, Accepted 15 Nov 1988, Published online: 04 Oct 2006

References

  • 1987 . Presented in a lecture at the Fourth European Carbohydrate Symposium . July 12–17 1987 , Darmstadt.
  • Rexen , F. and Munck , L. 1984 . Cereal Crops for Industrial Use in Europe , Denmark : EEC and Carlsberg Research Laboratory .
  • U. S. 3. 059. 011 . 1962 . Procter and Gamble; U.S. 4.614.718 (1986) Dai-Ichio Kogyo Seiyaka Co.; G. P. Rizzi and H. M. Taylor, J. Am. Oil. Chem. Soc., 55, 398 (1978); N. B. Desai and N. Lowicki, Parfümerie u. Kosmetik, 64, 463 (1983).
  • Putnik , C. F. and Borys , N. F. 1986 . Soap. Cos. Chem. Spec. , June A. D. Urfer, A. H. Malik, H. L. Kickle, G. M. Howell and N. F. Borys, Second World Conference on Detergents, p. 268, Montreux (1986).
  • Haferburg , D. , Hommel , R. , Claus , R. and Kleber , H.-P. 1986 . Adv. Biochem. Engineer , 33 : 55 P. A. Sandford, I. W. Cottrell and D. J. Pettitt, Pure & Appl. Chem., 56, 879 (1984). I. C. M. Dea and J. K. Madden, in: New Developments in Industrial Polysaccharides (V. Crescenzi, I. C. M. Dea and S. S. Stivala (Eds.)), p. 27, Gordon and Breach Publ., New York (1984).
  • Griffin , W. C. 1949 . J. Soc. Cosmet. Chem. , 1 : 311
  • Swisher , R. D. 1987 . Surfactant Biodegradation , New York : Marcel Dekker Inc. .
  • Borgström , B. and Brockman , H. L. 1984 . Lipases , Amsterdam : Elsevier .
  • Klibanov , A. M. 1986 . Chem. Tech. , : 355
  • Kamphuis , J. , Kloosterman , M. , Boesten , W. H. J. , Schoemakar , H. E. and Meijer , E. M. 1987 . Proc. IVth Eur. Congr. Biotechnol. , Edited by: Neijssel , O. M. , van der Meer , R. R. and Luyben , K. Ch. A. M. Vol. 4 , 331 – 348 . Amsterdam : Elsevier .
  • Kloosterman , M. , Mosmuller , E. W. J. , Schoemaker , H. E. and Meijer , E. M. 1987 . Tetrahedron Lett. , 28 : 2989
  • Cerny , M. and Stanek , J. Jr. 1977 . Adv. Carbohydr. Chem. Biochem. , 34 : 23 For a review on 1, 6-anhydroaldohexopyranoses, see, See alsoM. Kloosterman, M. J. Dees, G. A. van der Marel and J. H. van Boom, Recl. Trav. Chim. Pays-Bas, 104, 116 (1985); M. Kloosterman, M. P. de Nijs and J. H. van Boom, J. Carbohydr. Chem., 5, 215 (1986).
  • Lipases from Chromobacterium viscosum (L-0763), Candida cylindracea (L-1754), porcine pancreas (L-3126), wheat germ (L-3001) and esterase from porcine liver (E-3128) were purchased from Sigma Chemical Co. (of St. Louis). Mucor miehei lipase (SP 225) and experimental esterase (SP 122) were gifts from NOVO Industries (Kopenhagen). Lipase from a Pseudomonas strain (lipase P) was kindly provided by Amano Pharmaceutical Co.
  • No acyl migration was noted when compound (5) was stirred for two days in aqueous buffer (pH 7. 5) or when catalytic amounts of acid or base were added.
  • Csuk , R. and Glänzer , B. Zeitschr. Naturforsch. , The regioselective lipase-catalysed hydrolyses of acyl esters on 1, 6-anhydro-β-D-glycopyranoses has been further investigated by others. For acetyl esters see e. g., accepted for publication (private communication), and M. Martin-Lomas (private comm.). See also:, J. Zamek, K. Kucar and D. Anderle, Coll. Czech Chem. Commun., 52, 2347 (1987).
  • Fink , A. L. and Hay , G. W. 1969 . Can. J. Biochem. , 47 : 353
  • Shaw , J. F. and Klibanov , A. M. 1987 . Biotechnol. Bioengin. , 29 : 648
  • Kucár , S. , Zámocký , J. , Zemek , J. , Anderle , D. and Matulová , M. 1984 . Coll. Czech. Chem. Commun. , 49 : 1780
  • Borgström , B. and Brockman , H. L. , eds. 1984 . Lipases , Amsterdam : Elsevier . For reactions, in which insoluble substrates form aggregates surrounded by water, the reaction rate was found to be a function of the surface area of the substrate aggregate accessible to the enzyme. See
  • Kloosterman , M. , de Vries , N. K. , Schoemaker , H. E. and Meijer , E. M. 1988 . XIV Int. Carbohydr. Symp. August 14–19 1988 . pp. D – 36 . Stockholm : Abst. .
  • Kloosterman , M. , Elferink , V. E. , van Iersel , I. , Roskam , J. H. , Meijer , E. M. , Hulshof , L. and Sheldon , R. A. Trends in Biotechnology , in press.
  • Kloosterman , M. , Weijnen , J. G. J. , de Vries , N. K. , Mentech , J. , Caron , I. , Descotes , G. , Schoemaker , H. E. and Meijer , E. M. J. Carbohydr. Chem. , this volume.

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