124
Views
1
CrossRef citations to date
0
Altmetric
Research Article

Ketoreductase activity for reduction of substituted-β-tetralones utilizing aqueous-organic systems and β-cyclodextrin derivatives

&
Pages 226-237 | Received 13 Mar 2011, Accepted 28 Jan 2012, Published online: 07 Mar 2012

References

  • Almarsson O, Klibanov AM. 1996. Remarkable activation of enzymes in nonaqueous media by denaturing organic cosolvents. Biotechnol Bioeng 49:87–92.
  • Bekos EJ, Gardella JA, Bright FV. 1996. The binding of free oligopeptides to cyclodextrins: the role of the tyrosine group. J Incl Phenom Mol Recogn Chem 26:185–195.
  • Begue JP, Carceau C, Dogbeavou A, Mathe L, Sicsic S. 1992. Asymmetric microbial reduction of tetralones. J Chem Soc Perkin Trans I:3141–3144.
  • Brink LES, Tramper J. 1985. Optimiation of organic solvent in multiphase biocatalysis. Biotechnol Bioeng 27:1258–1269.
  • Chamani J, Moosavi-Movahedi AA, Hakimelahi GH. 2005. Structural changes in β-lactoglobulin by conjugation with three different kinds of carboxymethyl cyclodextrins. Thermochim Acta 432:106–111.
  • Chen YH, Yang JT, Martinez HM. 1972. Determination of the secondary structures of proteins by circular dichroism and optical rotatory dispersiont. Biochem 11:4120.
  • Clemente IM, Alvira E, Macias M, Ferrer A, Fonceca M, Rodriguez J, Gonzales A, Barletta G. 2002. Enzyme activation in organic solvents: co-lyophilization of subtilisinn carlsberg with methyl-β-cyclodextrin renders an enzyme catalyst more active than the cross-linked enzyme crystals. Biotechnol Bioeng 78:53–59.
  • Echstein M, Filho MV, Liese A, Kragl U. 2004. Use of an ionic liquid in a two-phase system to improve an alcohol dehydrogenase catalysed reduction. Chem Commun 1084–1085.
  • Faber K. 1997. Biotransformations in organic chemistry, 3rd ed. Berlin: Springer-Verlag.
  • Gao H, Wang YN, Fan YG, Ma JB. 2006. Interactions of some modified mono- and bis-b-cyclodextrins with bovine serum albumin. Bioorg Med Chem 14:131–137.
  • Ghanem A. 2003. The utility of cyclodextrins in lipase-catalyzed transesterification in organic solvents: enhanced reaction rate and enantioselectivity. Org Biomol Chem 1:1282–1291.
  • de Gonzalo G, Lavendera I, Faber K, Kroutil W. 2007. Enzymatic reduction of ketones in “Micro-aqueous” media catalyzed by ADH-A from Rhodococcus ruber. Org Lett 9: 2163–2166.
  • Gröger H, Hummel W, Buchholz S, Drauz K, Nguyen TV, Rollmann C, Husken H, Abokitse K. 2003. Preparative asymmetric reduction of ketones in a biphasic medium with an (S)-alcohol dehydrogenase under in situ-cofactor-recycling with a formate dehydrogenase. Org Lett 5:173–176.
  • Iwai J, Ogave N, Nagase H, Endo T, Loffsson T, Ueda H. 2007. Effects of various cyclodextrins on the stability of freeze-dried lactate dehydrogenase. J Pharm Sci 96:3140–3143.
  • Kaluzna IA, Rozzell J, Kambourakis S. 2005. Ketoreductases: stereoselective catalysts for the facile synthesis of chiral alcohols. Tetrahedron: Asymm 16:3682–3689.
  • Kambourakis S, Rozell JD. 2004. Ketoreductases in the synthesis of valuable chiral intermediates: application in the synthesis of α-hydroxy β-amino and β-hydroxy γ-amino acids. Tetrahedron 60:663–669.
  • Kelly DR, Lewis JD J. 1991. Unusual stereoselectivity in the reduction of bicyclo[3.3.0]oct-2-en-8-one by Thermoanaerobium brockii Alcohol dehydrogenase. Chem Soc Chem Comm 1330–1332.
  • Lee GL, Whitesides GM. 1985. Enzyme-catalyzed organic synthesis: a comparison of strategies for in situ regeneration of NAD from NADH. J Am Chem Soc 107:6999–7008.
  • Mogi M, Fuji K, Node M. 2004. Asymmetric reduction of methoxy substituted β-tetralones using transfer hydrogenation. Tetrahedron: Asymm 15:3715–3717.
  • Musa MM, Ziegelmann-Fjeld KI, Vieile C, Zeikus JG, Phillips, RS. 2007. Xerogel-encapsulated W110A secondary Alcohol dehydrogenase from Thermoanaerobacter ethanolicus performs asymmetric reduction of hydrophobic ketones in organic solvents. Angew Chem Int Ed Engl. 46:3091–3094.
  • Olofsson O, Nicholls IA, Wikman S. 2005. TbADH activity in water-miscible organic solvents: correlations between enzyme performance, enantioselectivity and protein structure through spectroscopic studies. Org Biomol Chem 3:750–755.
  • Park KK, Sim WJ, Park JW. 1996. Asymmetric induction by β-Cyclodextrons in NaBH4 reduction of ketones. J Inc Phen Mol Recogn Chem 27:41–48.
  • Sasaki T, Kobayashi M, Kise H. 1997. Active conformation of α-chymotrypsin in organic solvents as studied by circular dichroism. Biotechnol Tech 11:387–390.
  • Schneider HJ, Hacket F, Rudiger V, Ikeda H. 1998. NMR studies of cycllodextrins and cyclodextrin complexes. Chem Rev 98: 1755–1785.
  • Singh M, Sharma R, Banerjee UC. 2002. Biotechnological applications of cyclodextrins. Biotechnol Adv 20:341–359.
  • Skolen LG, Warnqvist B. 1969. Ark Kemi 31:377.
  • Soni P, Banerjee UC. 2006. Purification and characterization of an enantioselective carbonyl reductase from Candida viswanathii MTCC 5158. Biotechnol J 1:80–85.
  • Sundd M, Kundu S, Dubey VK, Jagannadham MV. 2004. Unfolding of Ervatamin C in the presence of organic solvents: sequential transitions of the protein in the O-state. J Biochem Mol Biol 37:586–596.
  • Swizdor A, Kolek T. 2009. Asymmetric reduction of tetralones and their methoxy derivatives by Fusarium culmorum. Biocatal Biotransformation 27:179–185.
  • Yang H, Jonsson A, Wehtje E, Adlercreutz P, Mattiasson B. 1997. The enantiomeric purity of alcohols formed by enzymatic reduction of ketones can be improved by optimisation of the temperature and by using a high co-substrate concentration. Biochim Biophys Acta 1336:51–58.
  • Yadav JS, Reddy GSKK, Sabitha G, Krishna AD, Prasat AR, Rahaman HUR, Rao KV, Rao AB. 2007. Daucus carota and baker's yeast mediated bio-reduction of prochiral ketones. Tetrahedron: Asymm 18:717–723.
  • Yamamoto T, Fukui N, Hori A, Matsui Y. 2002. Circular dichroism and fluorescence spectroscopy studies of the effect of cyclodextrins on the thermal stability of chicken egg white lysozyme in aqueous solution. J Mol Str 782:60–66.
  • Zelinski T, Liese A, Wandrey C, Kula MR. 1990. Asymmetric reductions in aqueous media: enzymatic synthesis in cyclodextrin containing buffers. Tetrahedron: Asymm 10:1681–1687.
  • Zhang HX, Huang X, Zhang M. 2008. Thermodynamic studies on the interaction of dioxopromethazine to β-cyclodextrin and bovine serum albumin. J Fluoresc 18:753–760.
  • Zhu D, Rios BE, Rozzell JD, Hua L. 2005. Evaluation of substituent effects on activity and enantioselectivity in the enzymatic reduction of aryl ketones. Tetrahedron: Asymm 16:1541–1546.
  • Zhu D, Yang Y, Buynak JD, Hua L. 2006. Stereoselective ketone reeduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme-substrate docking studies. Org Biomol Chem 4:2690–2695.
  • Zhu X, Sun J, Wu J. 2007a. Study on the inclusion interactions of β-cyclodextrin and its derivative with dyes by spectrofluorimetry and its analytical application. Talanta 72:237–242.
  • Zhu X, Sun J, Hu Y. 2007b. Determination of protein by hydroxypropyl-β-cyclodextrin sensitized fluorescence quenching method with erythrosine sodium as a fluorescence probe. Anal Chim Acta 596:298–302.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.