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Biocatalysis Volume 6, 1992 - Issue 2
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Original Article

Fatty Acid Specificity in Lipase-Catalyzed Synthesis of Glucoside Esters

Ole Kirk Novo Nordisk, Novo Allé, DK-2880, Bagsvaerd, Denmark
,
Fredrik Björkling Novo Nordisk, Novo Allé, DK-2880, Bagsvaerd, Denmark
,
Sven E. Godtfredsen Novo Nordisk, Novo Allé, DK-2880, Bagsvaerd, Denmark
&
Thomas Ostenfeld Larsen Novo Nordisk, Novo Allé, DK-2880, Bagsvaerd, Denmark
Pages 127-134 | Received 14 Aug 1991, Accepted 09 Jan 1992, Published online: 11 Jul 2009

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Emily M. Anderson, Karin M. Larsson & Ole Kirk. (1998) One Biocatalyst–Many Applications: The Use of Candida Antarctica B-Lipase in Organic Synthesis. Biocatalysis and Biotransformation 16:3, pages 181-204.
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Irina Yu. Yanina, Yulia I. Svenskaya, Ekaterina S. Prikhozhdenko, Daniil N. Bratashov, Maria V. Lomova, Dmitry A. Gorin, Gleb B. Sukhorukov & Valery V. Tuchin. (2018) Optical monitoring of adipose tissue destruction under encapsulated lipase action. Journal of Biophotonics 11:11.
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Alessandro Pellis, James W. Comerford, Andrew J. Maneffa, Mika H. Sipponen, James H. Clark & Thomas J. Farmer. (2018) Elucidating enzymatic polymerisations: Chain-length selectivity of Candida antarctica lipase B towards various aliphatic diols and dicarboxylic acid diesters. European Polymer Journal 106, pages 79-84.
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Daniel A. Sánchez, Gabriela M. Tonetto & María L. Ferreira. (2017) Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions . Biotechnology and Bioengineering 115:1, pages 6-24.
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Ashok Kumar, Kartik Dhar, Shamsher Singh Kanwar & Pankaj Kumar Arora. (2016) Lipase catalysis in organic solvents: advantages and applications. Biological Procedures Online 18:1.
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Joseph M. Griffin, John H. Atherton, Michael I. Page & Nicholas T. Powles. (2016) Lipase catalysed conversion of triglycerides to amides in liquid ammonia. Journal of Physical Organic Chemistry 29:12, pages 768-772.
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Elyse Champagne, Satu Strandman & Xiao-Xia Zhu. (2016) Recent Developments and Optimization of Lipase-Catalyzed Lactone Formation and Ring-Opening Polymerization. Macromolecular Rapid Communications 37:24, pages 1986-2004.
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Abhishek Singh, Remi Nguyen, Nicolas Galy, Rainer Haag, Sunil Sharma & Christophe Len. (2016) Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives. Molecules 21:8, pages 1038.
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J. M. Eby & S. W. Peretti. (2015) Performance in synthetic applications of a yeast surface display-based biocatalyst. RSC Advances 5:39, pages 30425-30432.
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Mark B. Frampton & Paul M. Zelisko. (2014) Chain length selectivity during the polycondensation of siloxane-containing esters and alcohols by immobilized Candida antarctica lipase B. Enzyme and Microbial Technology 58-59, pages 87-92.
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Shivika Sharma & Shamsher S. Kanwar. (2014) Organic Solvent Tolerant Lipases and Applications. The Scientific World Journal 2014, pages 1-15.
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Tim D. Nalder, Susan Marshall, Frederick M. Pfeffer & Colin J. Barrow. (2014) Characterisation of lipase fatty acid selectivity using novel omega-3 pNP-acyl esters. Journal of Functional Foods 6, pages 259-269.
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Mark B. Frampton & Paul M. Zelisko. (2013) Synthesis of lipase-catalysed silicone-polyesters and silicone-polyamides at elevated temperatures. Chemical Communications 49:81, pages 9269.
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Katherine Nott, Gaëtan Richard, Pascal Laurent, Christine Jérôme, Christophe Blecker, Jean-Paul Wathelet, Michel Paquot & Magali Deleu. (2013) Enzymatic synthesis and surface properties of novel rhamnolipids. Process Biochemistry 48:1, pages 133-143.
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Soundar DivakarSoundar Divakar. 2013. Enzymatic Transformation. Enzymatic Transformation 81 122 .
Soundar DivakarSoundar Divakar. 2013. Enzymatic Transformation. Enzymatic Transformation 23 38 .
Cecilia Orellana Åkerman, Yasser Gaber, Noraini Abd Ghani, Merja Lämsä & Rajni Hatti-Kaul. (2011) Clean synthesis of biolubricants for low temperature applications using heterogeneous catalysts. Journal of Molecular Catalysis B: Enzymatic 72:3-4, pages 263-269.
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Le Qian, Jia-Yan Liu, Jia-Ying Liu, Hui-Lei Yu, Chun-Xiu Li & Jian-He Xu. (2011) Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids. Journal of Molecular Catalysis B: Enzymatic.
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P.B. Juhl, K. Doderer, F. Hollmann, O. Thum & J. Pleiss. (2010) Engineering of Candida antarctica lipase B for hydrolysis of bulky carboxylic acid esters. Journal of Biotechnology 150:4, pages 474-480.
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Robert Chênevert, Nicholas Pelchat & Pierre Morin. (2009) Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications. Tetrahedron: Asymmetry 20:10, pages 1191-1196.
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Hyuk-Seong Seo, Seong-Eun Kim, Kyung-Yeon Han, Jin-Seung Park, Yong-Hwan Kim, Sang Jun Sim & Jeewon Lee. (2009) Functional fusion mutant of Candida antarctica lipase B (CalB) expressed in Escherichia coli. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1794:3, pages 519-525.
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Ning Li, Min‐Hua Zong & Ding Ma. (2008) Regioselective Acylation of Nucleosides Catalyzed by Candida Antarctica Lipase B: Enzyme Substrate Recognition . European Journal of Organic Chemistry 2008:32, pages 5375-5378.
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Jesper Brask. 2008. The Power of Functional Resins in Organic Synthesis. The Power of Functional Resins in Organic Synthesis 365 380 .
M. Verma, W. Azmi & S. Kanwar. (2008) Microbial lipases: At the interface of aqueous and non-aqueous media. Acta Microbiologica et Immunologica Hungarica 55:3, pages 265-294.
Crossref
Bo Chen, Jun Hu, Elizabeth M. Miller, Wenchun Xie, Minmin Cai & Richard A. Gross. (2008) Candida antarctica Lipase B Chemically Immobilized on Epoxy-Activated Micro- and Nanobeads: Catalysts for Polyester Synthesis . Biomacromolecules 9:2, pages 463-471.
Crossref
Bo Chen, M. Elizabeth Miller & Richard A. Gross. (2007) Effects of Porous Polystyrene Resin Parameters on Candida antarctica Lipase B Adsorption, Distribution, and Polyester Synthesis Activity . Langmuir 23:11, pages 6467-6474.
Crossref
Kenchaiah Lohith & Soundar Divakar. (2007) Candida rugosa lipase catalysed preparation of l-prolyl, l-phenylalanyl, l-tryptophanyl and l-histidyl esters of carbohydrates. Biochemical Engineering Journal 34:1, pages 28-43.
Crossref
Bhandya R. Somashekar & Soundar Divakar. (2007) Lipase catalyzed synthesis of l-alanyl esters of carbohydrates. Enzyme and Microbial Technology 40:2, pages 299-309.
Crossref
Kerstin Blank, Julia Morfill, Hermann Gumpp & Hermann E. Gaub. (2006) Functional expression of Candida antarctica lipase B in Eschericha coli. Journal of Biotechnology 125:4, pages 474-483.
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K. Lohith, G.R. Vijayakumar, B.R. Somashekar, R. Sivakumar & S. Divakar. (2006) Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme. European Journal of Medicinal Chemistry 41:9, pages 1059-1072.
Crossref
Xiang-Guo Zhao, Dong-Zhi Wei & Qing-Xun Song. (2005) A facile enzymatic process for the preparation of ibuprofen ester prodrug in organic media. Journal of Molecular Catalysis B: Enzymatic 36:1-6, pages 47-53.
Crossref
Takahiko NakaokiYing MeiLisa M. MillerAjay KumarBhanu KalraM. Elizabeth MillerOle KirkMorten ChristensenRichard A. Gross. (2005) Candida antarctica lipase B catalyzed polymerization of lactones: Effects of immobilization matrices on polymerization kinetics & molecular weight . Industrial Biotechnology 1:2, pages 126-134.
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Kenchaiah Lohith & Soundar Divakar. (2005) Lipase-catalyzed synthesis of l-phenylalanyl-d-glucose. Journal of Biotechnology 117:1, pages 49-56.
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Yeon Soo Lee, Joo Hee Hong, Nan Young Jeon, Keehoon Won & Bum Tae Kim. (2004) Highly Enantioselective Acylation of rac -Alkyl Lactates Using Candida antarctica Lipase B . Organic Process Research & Development 8:6, pages 948-951.
Crossref
Richard.W. McCabe & Alan Taylor. (2004) An investigation of the acyl-binding site of Candida antarctica lipase B. Enzyme and Microbial Technology 35:5, pages 393-398.
Crossref
X Fu & K.L Parkin. (2004) Selectivity of fatty acid incorporation into acylglycerols in esterification reactions using Rhizomucor miehei and Burkholderia cepacia lipases. Food Research International 37:7, pages 651-657.
Crossref
Xun Fu & Kirk L. Parkin. (2004) Reaction selectivity of rhizomucor miehei lipase as influenced by monoacylation of sn -glycerol . Journal of the American Oil Chemists' Society 81:1, pages 45.
Crossref
Xun Fu & Kirk L. Parkin. (2004) Reaction selectivity of Burkholderia cepacia (PS-30) lipase as influenced by monoacylation of sn -glycerol . Journal of the American Oil Chemists' Society 81:1, pages 33.
Crossref
Olga V. Oskolkova, Robert Saf, Elfriede Zenzmaier & Albin Hermetter. (2003) Fluorescent organophosphonates as inhibitors of microbial lipases. Chemistry and Physics of Lipids 125:2, pages 103-114.
Crossref
Dongzhi Wei, Chunang Gu, Qingxun Song & Wu Su. (2003) Enzymatic esterification for glycoside lactate synthesis in organic solvent. Enzyme and Microbial Technology 33:4, pages 508-512.
Crossref
Ying Mei, Lisa Miller, Wei Gao & Richard A. Gross. (2002) Imaging the Distribution and Secondary Structure of Immobilized Enzymes Using Infrared Microspectroscopy. Biomacromolecules 4:1, pages 70-74.
Crossref
Ole Kirk & Morten Würtz Christensen. (2002) Lipases from Candida a ntarctica : Unique Biocatalysts from a Unique Origin . Organic Process Research & Development 6:4, pages 446-451.
Crossref
Maria Victoria Flores, Kaynoush Naraghi, Jean‐Marc Engasser & Peter J. Halling. (2002) Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2‐methyl 2‐butanol. Biotechnology and Bioengineering 78:7, pages 815-821.
Crossref
Armando Córdova. (2001) Synthesis of Amphiphilic Poly(ε-caprolactone) Macromonomers by Lipase Catalysis. Biomacromolecules 2:4, pages 1347-1351.
Crossref
Romas J. Kazlauskas & Uwe T. Bornscheuer. 2001. Biotechnology Set. Biotechnology Set 37 191 .
Jad Arsan & Kirk L. Parkin. (2000) Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media . Journal of Agricultural and Food Chemistry 48:8, pages 3738-3743.
Crossref
Carlos Torres, Manuel Bernabé & Cristina Otero. (1999) Part II. Two enzymatic procedures for the selective synthesis of malic acid monoesters. Enzyme and Microbial Technology 25:8-9, pages 753-761.
Crossref
Carlos Torres & Cristina Otero. (1999) Part I. Enzymatic synthesis of lactate and glycolate esters of fatty alcohols. Enzyme and Microbial Technology 25:8-9, pages 745-752.
Crossref
A. Córdova, T. Iversen & K. Hult. (1999) Lipase-catalyzed formation of end-functionalized poly(ϵ-caprolactone) by initiation and termination reactions. Polymer 40:24, pages 6709-6721.
Crossref
Marie-Pierre Bousquet, Ren�-Marc Willemot, Pierre Monsan & Emmanuel Boures. (1999) Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications. Biotechnology and Bioengineering 63:6, pages 730-736.
Crossref
Marie-Pierre Bousquet, René-Marc Willemot, Pierre Monsan & Emmanuel Boures. (1999) Lipase-catalyzed α-butylglucoside lactate synthesis in organic solvent for dermo-cosmetic application. Journal of Biotechnology 68:1, pages 61-69.
Crossref
Marie‐Pierre Bousquet, René‐Marc Willemot, Pierre Monsan & Emmanuel Boures. (2000) Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative. Biotechnology and Bioengineering 62:2, pages 225-234.
Crossref
Miguel Arroyo, José Marı́a Sánchez-Montero & José Vicente Sinisterra. (1999) Thermal stabilization of immobilized lipase B from Candida antarctica on different supports: Effect of water activity on enzymatic activity in organic media. Enzyme and Microbial Technology 24:1-2, pages 3-12.
Crossref
S Patkar, J Vind, E Kelstrup, M.W Christensen, A Svendsen, K Borch & O Kirk. (1998) Effect of mutations in Candida antarctica B lipase. Chemistry and Physics of Lipids 93:1-2, pages 95-101.
Crossref
Jürgen Pleiss, Markus Fischer & Rolf D Schmid. (1998) Anatomy of lipase binding sites: the scissile fatty acid binding site. Chemistry and Physics of Lipids 93:1-2, pages 67-80.
Crossref
Romas J. Kazlauskas & Uwe T. Bornscheuer. 1998. Biotechnology. Biotechnology 36 191 .
M.C. de Zoete, A.C. Kock-van Dalen, F. van Rantwijk & R.A. Sheldon. (1996) Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides [J. Mol. Catal. B, 1 (1996) 109–113]. Journal of Molecular Catalysis B: Enzymatic 2:2-3, pages 141-145.
Crossref
M. C. DE ZOETE, A. C. KOCK-VAN DALEN, F. VAN RANTWIJK & R. A. SHELDON. (1996) Ammonolysis of Carboxylic Esters Catalyzed by Lipases.. Annals of the New York Academy of Sciences 799:1 Enzyme Engine, pages 346-350.
Crossref
M.C. de Zoete, A.C. Kock-van Dalen, F. van Rantwijk & R.A. Sheldon. (1996) Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides. Journal of Molecular Catalysis B: Enzymatic 1:3-6, pages 109-113.
Crossref
Victor M. Balcão, Ana L. Paiva & F. Xavier Malcata. (1996) Bioreactors with immobilized lipases: State of the art. Enzyme and Microbial Technology 18:6, pages 392-416.
Crossref
Oh-Jin Park, Hyun Gyu Park & Ji-Won Yang. (1996) Enzymatic transesterification of monosaccharides and amino acid esters in organic solvents. Biotechnology Letters 18:4, pages 473-478.
Crossref
S. Riva. 1996. Enzymatic Reactions in Organic Media. Enzymatic Reactions in Organic Media 140 169 .
Inge Høegh, Shamkant Patkar, Torben Halkier & Mogens T. Hansen. (1995) Two lipases from Candida antarctica : cloning and expression in Aspergillus oryzae . Canadian Journal of Botany 73:S1, pages 869-875.
Crossref
David Kwoh, David J. Pocalyko, Angel J. Carchi, Bijan Harirchian, Leonard O. Hargiss & Tuck C. Wong. (1995) Regioselective synthesis and characterization of 6-O-alkanoylgluconolactones. Carbohydrate Research 274, pages 111-121.
Crossref
Neena N. Gandhi, Sudhirprakash B. Sawant & Jyeshtharaj B. Joshi. (2008) Specificity of a Lipase in Ester Synthesis: Effect of Alcohol. Biotechnology Progress 11:3, pages 282-287.
Crossref
SHI-DE LIU, SHU-GUI CAO, ZHONG-TIAN DING, LING-FENG SUN, NIAN-XIANG ZHANG, QI-ZHI LIANG, HONG-HU LIU & HONG YANG. (1995) A New Method for Estimating the Selectivity of Lipases for Fatty Acids and Fatty Alcohols in Organic Solvents. Annals of the New York Academy of Sciences 750:1 Enzyme Engine, pages 209-214.
Crossref
G. B. Oguntimein, W. A. Anderson & M. Moo-Young. (1995) Synthesis of geraniol esters in a solvent-free system catalysed by Candida antarctica lipase. Biotechnology Letters 17:1, pages 77-82.
Crossref
Gudrun Ljunger, Patrick Adlercreutz & Bo Mattiasson. (1994) Lipase catalyzed acylation of glucose. Biotechnology Letters 16:11, pages 1167-1172.
Crossref
Raúl J. Barros, Pedro G.V. Moura-Pinto, Maurice C.R. Franssen, de Groot Aede & Anja E.M. Janssen. (1994) Regioselectivity and fatty acid specificity of Chromobacterium viscosum lipase. Bioorganic & Medicinal Chemistry 2:7, pages 707-713.
Crossref
F. Björkling, S. E. Godtfredsen, O. Kirk, S. A. Patkar & O. Andresen. 1992. Microbial Reagents in Organic Synthesis. Microbial Reagents in Organic Synthesis 249 260 .

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