Pseudomonas cepacia lipase immobilized on Zn₂Al layered double hydroxides: Evaluation of different methods of immobilization for the kinetic resolution of (R,S)-1-phenylethanol

References

• Abdul Rahman MB, Zaidan UH, Basri M, Hussein MZ, Rahman R, Salleh AB. 2008. Enzymatic synthesis of methyl adipate ester using lipase from Candida rugosa immobilised on Mg, Zn and Ni of layered double hydroxides (LDHs). J Mol Catal B Enzym. 50(1):33–39.
   Google Scholar
• Adachi-Pagano M, Forano C, Besse J-P. 2000. Delamination of layered double hydroxides by use of surfactants. Chem Commun. 1(1):91–92.
   Google Scholar
• Aghaei H, Ghavi M, Hashemkhani G, Keshavarz M. 2020. Utilization of two modified layered doubled hydroxides as supports for immobilization of Candida rugosa lipase. Int J Biol Macromol. 162:74–83.
   PubMed Web of Science ®Google Scholar
• An Z, Lu S, He J, Wang Y. 2009. Colloidal assembly of proteins with delaminated lamellas of layered metal hydroxide. Langmuir. 25(18):10704–10710.
   PubMed Web of Science ®Google Scholar
• Anderson EM, Larsson KM, Kirk O. 1998. One biocatalyst – many applications: the use of Candida antarctica B-lipase in organic synthesis. Biocatal Biotransformation. 16(3):181–204.
   Web of Science ®Google Scholar
• Bandeira PT, Alnoch RC, De Oliveira ARM, De Souza EM, Pedrosa FdO, Krieger N, Piovan L. 2016. Enzymatic kinetic resolution of aliphatic sec-alcohols by LipG9, a metagenomic lipase. J Mol Catal B Enzym. 125:58–63.
   Google Scholar
• Barhoumi H, Maaref A, Rammah M, Martelet C, Jaffrezic N, Mousty C, Vial S, Forano C. 2006. Urea biosensor based on Zn3Al–Urease layered double hydroxides nanohybrid coated on insulated silicon structures. Mater Sci Eng C. 26(2–3):328–333.
   Google Scholar
• Benaissi K, Hélaine V, Prévot V, Forano C, Hecquet L. 2011. Efficient immobilization of yeast transketolase on layered double hydroxides and application for ketose synthesis. Adv Synth Catal. 353(9):1497–1509.
   Web of Science ®Google Scholar
• Bornscheuer UT, Kazlauskas RJ. 2006. Hydrolases in organic synthesis: regio- and stereoselective biotransformations. 2nd ed. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA.
   Google Scholar
• Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein–dye binding. Anal Biochem. 72:248–254.
   PubMed Web of Science ®Google Scholar
• Bruna F, Mousty C, Besse-Hoggan P, Batisson I, Prevot V. 2019. Assembly of nitroreductase and layered double hydroxides toward functional biohybrid materials. J Colloid Interface Sci. 533:71–81.
   PubMed Web of Science ®Google Scholar
• Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. 1982. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc. 104(25):7294–7299.
   Web of Science ®Google Scholar
• Dias MRG, De Pauloveloso A, Do Amaral LFM, Betim RT, Nascimento MG, Pilissão C. 2018. Immobilization of Burkholderia cepacia on pristine or functionalized multi-walled carbon nanotubes and application on enzymatic resolution of (R,S)-1-phenylethanol. J Braz Chem Soc. 29:1876–1884.
   Web of Science ®Google Scholar
• Djebbi MA, Braiek M, Hidouri S, Namour P, Jaffrezic-Renault N, Ben Haj Amara A. 2016. Novel biohybrids of layered double hydroxide and lactate dehydrogenase enzyme: synthesis, characterization and catalytic activity studies. J Mol Struct. 1105:381–388.
   Web of Science ®Google Scholar
• Dong H, Parekh HS, Xu ZP. 2015. Particle size- and number-dependent delivery to cells by layered double hydroxide nanoparticles. J Colloid Interface Sci. 437:10–16.
   PubMed Web of Science ®Google Scholar
• Dong L, Ge C, Qin P, Chen Y, Xu Q. 2014. Immobilization and catalytic properties of candida lipolytic lipase on surface of organic intercalated and modified MgAl–LDHs. Solid State Sci. 31:8–15.
   Web of Science ®Google Scholar
• Dulęb J, Michal TS, Marszall P. 2022. The influence of substrate systems on the enantioselective and lipolytic activity of immobilized Amano PS from Burkholderia cepacia lipase (APS-BCL). Process Biochem. 120:126–137.
   Web of Science ®Google Scholar
• Dwivedee BP, Soni S, Bhimpuria R, Laha JK, Banerjee UC. 2019. Tailoring a robust and recyclable nanobiocatalyst by immobilization of Pseudomonas fluorescens lipase on carbon nanofiber and its application in synthesis of enantiopure carboetomidate analogue. Int J Biol Macromol. 133:1299–1310.
   PubMed Web of Science ®Google Scholar
• Forano C, Vial S, Mousty C. 2006. Nanohybrid enzymes – layered double hydroxides: potential applications. CNANO. 2(3):283–294.
   Google Scholar
• Forano C. 2004. Environmental remediation involving layered double hydroxides. Interface Sci Technol. 1:425–458.
   Google Scholar
• Fouz MF, Sumanarathne AS, Seneviratne VN, Rajapakse S. 2021. Investigation of enhancement in thermal stability of trypsin in modified Mg/Al layered double hydroxides. Ceylon J Sci. 50(1):29–38.
   Google Scholar
• Frykman H, Öhrner N, Norin T, Hult K. 1993. S-ethyl thiooctanoate as acyl donor in lipase catalysed resolution of secondary alcohols. Tetrahedron Lett. 34(8):1367–1370.
   Web of Science ®Google Scholar
• Ghanem A, Aboul-Enein MN, El-Azzouny A, El-Behairy MF. 2010. Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses. J Chromatogr A. 1217(7):1063–1074.
   PubMed Web of Science ®Google Scholar
• Gondim DR, Cecilia JA, Santos SO, Rodrigues TNB, Aguiar JE, Vilarrasa-García E, Rodríguez-Castellón E, Azevedo DCS, Silva IJ. 2018. Influence of buffer solutions in the adsorption of human serum proteins onto layered double hydroxide. Int J Biol Macromol. 106:396–409.
   PubMed Web of Science ®Google Scholar
• He J, Wei M, Li B, Kang Y, Evans DG, Duan X. 2005. Preparation of layered double hydroxides. Berlin/Heidelberg: Springer-Verlag.
   Google Scholar
• Hibino T, Kobayashi M. 2005. Delamination of layered double hydroxides in water. J Mater Chem. 15(6):653.
   Web of Science ®Google Scholar
• Kazlauskas RJ, Weissfloch ANE, Rappaport AT, Cuccia LA. 1991. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J Org Chem. 56(8):2656–2665.
   Web of Science ®Google Scholar
• Klibanov AM. 2001. Improving enzymes by using them in organic solvents. Nature. 409(6817):241–246.
   PubMed Web of Science ®Google Scholar
• Kloprogge JT, Wharton D, Hickey L, Frost RL. 2002. Infrared and Raman study of interlayer anions CO32–, NO3–, SO42– and ClO4– in Mg/Al–hydrotalcite. Am Miner. 87(5–6):623–629.
   Web of Science ®Google Scholar
• Li K, Wang J, He Y, Cui G, Abdulrazaq MA, Yan Y. 2018. Enhancing enzyme activity and enantioselectivity of Burkholderia cepacia lipase via immobilization on melamine-glutaraldehyde dendrimer modified magnetic nanoparticles. Chem Eng J. 351:258–268.
   Web of Science ®Google Scholar
• Liu DM, Dong C. 2020. Recent advances in nano-carrier immobilized enzymes and their applications. Process Biochem. 92:464–475.
   Web of Science ®Google Scholar
• Melais N, Aribi-Zouioueche L, Riant O. 2016. The effect of the migrating group structure on enantioselectivity in lipase-catalyzed kinetic resolution of 1-phenylethanol. Comptes Rendus Chim. 19(8):971–977.
   Web of Science ®Google Scholar
• Mishra G, Dash B, Pandey S. 2018. Layered double hydroxides: a brief review from fundamentals to application as evolving biomaterials. Appl Clay Sci. 153:172–186.
   Web of Science ®Google Scholar
• Moure VR, Fabrício C, Frensch G, Marques FA, Mitchell DA, Krieger N. 2014. Enhancing the enantioselectivity of the lipase from Burkholderia cepacia LTEB11 towards the resolution of secondary allylic alcohols. Biocatal Agric Biotechnol. 3(2):146–153.
   Google Scholar
• Newman SP, Jones W. 1998. Synthesis, characterization and applications of layered double hydroxides containing organic guests. New J Chem. 22(2):105–115.
   Web of Science ®Google Scholar
• Ortiz C, Ferreira ML, Barbosa O, Dos Santos JCS, Rodrigues RC, Berenguer-Murcia Á, Briand LE, Fernandez-Lafuente R. 2019. Novozym 435: the “perfect” lipase immobilized biocatalyst? Catal Sci Technol. 9(10):2380–2420.
   Web of Science ®Google Scholar
• Rahman MBA, Basri M, Hussein MZ, Rahman R, Zainol DH, Salleh AB. 2004. Immobilization of lipase from Candida rugosa on layered double hydroxides for esterification reaction. Appl Biochem Biotechnol. 118(1–3):313–320.
   PubMed Web of Science ®Google Scholar
• Rahman MBA, Othman SS, Yunus NMM. 2016. Selectivity of Candida rugosa lipase immobilized onto layered double hydroxides as catalyst in synthesis of fatty acid esters. J Teknol. 5–6:111–115.
   Google Scholar
• Reichle WT. 1986. Synthesis of anionic clay minerals (mixed metal hydroxides, hydrotalcite). Solid State Ionics. 22(1):135–141.
   Web of Science ®Google Scholar
• Ren L, He J, Zhang S, Evans DG, Duan X. 2002. Immobilization of penicillin G acylase on calcined layered double hydroxides. Chem Res Chin Univ. 18(1–3):3–11.
   Google Scholar
• Show PL, Tan CP, Shamsul Anuar M, Ariff A, Yusof YA, Chen SK, Ling TC. 2012. Extractive fermentation for improved production and recovery of lipase derived from Burkholderia cepacia using a thermo separating polymer in aqueous two-phase systems. Bioresour Technol. 116:226–233.
   PubMed Web of Science ®Google Scholar
• Silva Dias G, Bandeira PT, Jaerger S, Piovan L, Mitchell DA, Wypych F, Krieger N. 2019. Immobilization of Pseudomonas cepacia lipase on layered double hydroxide of Zn/Al–Cl for kinetic resolution of rac-1-phenylethanol. Enzyme Microb Technol. 130(2019):109365.
   PubMedGoogle Scholar
• Silverstein RM, Webster FX, Kiemle DJ. 2005. Spectrometric identification of organic compounds. 7th ed. Hoboken, NJ: Wiley.
   Google Scholar
• Stepankova V, Bidmanova S, Koudelakova T, Prokop Z, Chaloupkova R, Damborsky J. 2013. Strategies for stabilization of enzymes in organic solvents. ACS Catal. 3(12):2823–2836.
   Web of Science ®Google Scholar
• Strauss UT, Felfer U, Faber K. 1999. Biocatalytic transformation of racemates into chiral building blocks in 100% chemical yield and 100% enantiomeric excess. Tetrahedron Asymmetry. 10(1):107–117.
   Google Scholar
• Tahsiri Z, Niakousari M, Hosseini SMH, Majdinasab M. 2022. Magnetic layered double hydroxide nanosheet as a biomolecular vessel for enzyme immobilization. Int J Biol Macromol. 209(Pt A):1422–1429.
   PubMedGoogle Scholar
• Tasnádi G, Forró E, Fülöp F. 2009. Burkholderia cepacia lipase is an excellent enzyme for the enantioselective hydrolysis of β-heteroaryl-β-amino esters. Tetrahedron Asymmetry. 20(15):1771–1777.
   Google Scholar
• Taviot-Guého C, Prévot V, Forano C, Renaudin G, Mousty C, Leroux F. 2018. Tailoring hybrid layered double hydroxides for the development of innovative applications. Adv Funct Mater. 28(27):1703868.
   Web of Science ®Google Scholar
• Tiss A, Carrière F, Verger R. 2001. Effects of gum arabic on lipase interfacial binding and activity. Anal Biochem. 294(1):36–43.
   PubMed Web of Science ®Google Scholar
• Vaccari A. 2001. Layered double hydroxides: present and future. New York: Nova Science Publishers, Inc.
   Google Scholar
• Wang J, Bao W, Umar A, Wang Q, O'Hare D, Wan Y. 2016. Delaminated layered double hydroxide nanosheets as an efficient vector for DNA delivery. J Biomed Nanotechnol. 12(5):922–933.
   PubMed Web of Science ®Google Scholar
• Wang M, Bao W, Wang J, Wang K, Xu J, Chen H, Xia X. 2014. A green approach to the synthesis of novel “Desert rose stone”-like nanobiocatalytic system with excellent enzyme activity and stability. Sci Rep. 4:6606.
   PubMed Web of Science ®Google Scholar
• Xu ZP, Stevenson G, Lu CQ, Lu GQ. 2006. Dispersion and size control of layered double hydroxide nanoparticles in aqueous solutions. J Phys Chem B. 110(34):16923–16929.
   PubMed Web of Science ®Google Scholar
• Yu J, Wang Q, O'Hare D, Sun L. 2017. Preparation of two dimensional layered double hydroxide nanosheets and their applications. Chem Soc Rev. 46(19):5950–5974.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Li F, Zhang R, Evans DG, Duan X. 2002. Preparation of layered double-hydroxide nanomaterials with a uniform crystallite size using a new method involving separate nucleation and aging steps. Chem Mater. 14(10):4286–4291.
   Web of Science ®Google Scholar
• Zheng M, Xiang X, Wang S, Shi J, Deng Q, Huang F, Cong R. 2017. Lipase immobilized in ordered mesoporous silica: a powerful biocatalyst for ultrafast kinetic resolution of racemic secondary alcohols. Process Biochem. 53:102–108.
   Web of Science ®Google Scholar
• Zhu Y, Rong J, Zhang T, Xu J, Dai Y, Qiu F. 2018. Facile and controlled fabrication of Cu–Al layered double hydroxide nanosheets/laccase hybrid films: a route to efficient biocatalytic removal of Congo Red from aqueous solutions. ACS Appl Nano Mater. 1(1):284–292.
   Web of Science ®Google Scholar