Laccase activity and stability in the presence of menthol - based ionic liquids

• Autorzy: Fader-Kubis J. , Bryjak J.
• Języki publikacji: EN

Abstrakty

EN

Laccases attract attention due to their potential for manufacturing pharmaceutical intermediates from a wide array of phenolic and non-phenolic substrates that are sparingly soluble in water. Because of the high polarity of ionic liquids (ILs), they can dissolve polar and nonpolar compounds and are claimed as "green" alternative for volatile organic solvents. The main aim of this work was to find water-immiscible ILs suitable for Cerrena unicolor laccase. For that five ILs with bis(trifluoromethanesulfonyl)imide anions coupled with cations derived from natural alcohol - (1R,2S,5R)-(-)-menthol were synthesized, namely: (I) 3-butyl-1-[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium, (II) 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-heptylimidazolium, (III) 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylpyridinium, (IV) heptyl[(1R,2S,5R)-(-)-menthoxymethyl]dimethylammonium, and (V) decyl[(1R,2S,5R)-(-)-menthoxymethyl]dimethylammonium ions. Laccase activity was tested in buffer saturated with ILs whereas stability tests in biphasic systems lasted 5 days. It was shown that ILs I, III-V did not significantly alter laccase activity (being 90-123% respective to the buffer) whereas IL II decreased reactivity in 20%. Stability tests revealed that ILs I, IV and V increased enzyme stability even more than in the buffer. For mathematical formalization of inactivation courses, isoenzyme model was applied but this model fitted experimental data only for sets obtained in the buffer (control) and in the presence of IL II. In the other cases, first-order reaction model was sufficient. This shows that ILs, even at very low concentrations, influence conformational stability of proteins, which is dependent on the cation structure. In general, the imidazolium (I) and ammonium (IV) salts with shorter alkyl chains supported laccase activity and stability.

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2013
• Tom: 60
• Numer: 4
• Opis fizyczny: p.741-745,fig.,ref.

Twórcy

autor

Fader-Kubis J.

• Wrocław University of Technology, Faculty of Chemistry, Department of Chemical Engineering, Wroclaw, Poland

autor

Bryjak J.

• Wrocław University of Technology, Faculty of Chemistry, Department of Bioorganic Chemistry, Wroclaw, Poland

Bibliografia

• Al-Adhami AJH, Bryjak J, Greb-Markiewicz B, Peczyńska-Czoch W (2002) Immobilization of wood-rotting fungi laccases on modified cellulose and acrylic carriers. Process Biochem 37: 1387-1394.
• Bryjak J, Rekuć A (2010) Effective purification of Cerrena unicolor laccase using microfiltration, ultrafiltration and acetone precipitation. Appl Biochem Biotechnol 160: 2219-2235. 
• Childs RE, Bardsley WG (1975) The steady-state kinetics of peroxidase with 2,20-azino-di-(3-ethyl-benzthiazoline-6-sulphonic acid) as chromogen. Biochem J 145: 93-103. 
• Liese A, Seelbach K, Wandrey C, eds (2006) Industrial Biotransformations. WILEY-VCH, Verlag GmbH & Co., Weinheim. 
• Michniewicz A, Ullrich R, Ledakowicz S, Hofrichter M (2006) The white-rot fungus Cerrena unicolor strain 137 produces two laccase isoforms with different physico-chemical and catalytic properties. Appl Microbiol Biotechnol 69: 682-688. 
• Mikolasch A, Schauer F (2009) Fungal laccases as tools for the synthesis of new hybrid molecules and biomaterials. Appl Microbiol Biotechnol 82: 605-624. 
• Moniruzzaman M, Nakashima K, Kamiya N, Goto M (2010) Recent advances of enzymatic reactions in ionic liquids. Biochem Eng J 48: 295-314.
• Pernak J, Feder-Kubis J (2005) Synthesis and properties of chiral ammonium-based ionic liquids. Chem Eur J 11: 4441-4449. 
• Pernak J, Feder-Kubis J (2006) Chiral pyridinium-based ionic liquids containing the (1R,2S,5R)-(-)-menthyl group. Tetrahedron Asymmetr 17: 1728-1737.
• Pernak J, Feder-Kubis J, Cieniecka-Rosłonkiewicz A, Fischmeister C, Griffin ST, Rogers RD (2007) Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(-)-menthoxymethyl substituent. New J Chem 31: 879-892.
• Pinto PC, Saraiva ML, Lima JL (2008) Oxidoreductase behavior in ionic liquids: A review. Anal Sci 24: 1231-1238. 
• Polak J, Jarosz-Wilkołazka A (2012) Fungal laccases as green catalysts for dye synthesis. Process Biochem 47: 1295-1307.
• Polakovič M, Vrábel P (1996) Analysis of the mechanism and kinetics of thermal inactivation of enzymes: Critical assessment of isothermal inactivation experiments. Process Biochem 31: 787-800.
• Rehmann L, Ivanova E, Ferguson JL, Gunaratne HQN, Seddon KR, Stephens GM (2012) Mesuring the effect of ionic liquids on laccase activity using a simple, parallel method. Green Chem 14: 725-733.
• Rodriguez O, Cristovão RO, Tavares AP, Macedo EA (2011) Study of the alkyl chain length on laccase stability and enzymatic kinetic with imidazolium ionic liquid. Appl Biochem Biotechnol 164: 524-533. 
• Ross AC, Bell G, Halling PJ (2000) Organic solvent functional group effect on enzyme inactivation by the interfacial mechanism. J Mol Catal B: Enzym 8: 183-192.
• Sadana A., ed. (1991) Biocatalysis: Fundamentals of Enzyme Deactivation. Prentice Hall, New Jersey. 
• Shipovskov S, Gunaratne N, Seddon KR, Stephens G (2008) Catalytic activity of laccases in aqueous solutions of ionic liquids. Green Chem 10: 806-810.
• Thomas CR, Geer D (2010) Effects of shear on proteins in solution. Biotechnol Lett 33: 443-456. 
• van Rantwijk F, Sheldon RA (2007) Biocatalysis in ionic liquids. Chem Rev 107: 2757-2758 
• Witayakran S, Ragauskas AJ (2009) Synthetic applications of laccase in green chemistry. Adv Synth Catal 351: 1187-1209.
• Xue L, Qiu H, Li Y, Lu L, Huang X, Qu Y (2011) A novel water-in-ionic liquid microemulsion and its interfacial effect on the activity of laccase. Colloids Surf B 82: 432-437. 
• Yang Z, Pan W (2005) Ionic liquids: Green solvents for nonaqueous biocatalysis. Enzyme Microb Technol 37: 19-28.