Enzymes in Nonaqueous Solvents: Methods and Protocols

ISBN-13: 9781617372568 / Angielski / Miękka / 2010 / 679 str.

Evgeny N. Vulfson

Opis

Enzymatic catalysis has gained considerable attention in recent years as an efficient tool in the preparation of natural products, pharmaceuticals, fine chemicals, and food ingredients. The high selectivity and mild reaction con- tions associated with enzymatic transformations have made this approach an attractive alternative in the synthesis of complex bioactive compounds, which are often difficult to obtain by standard chemical routes. However, the maj- ity of organic compounds are not very soluble in water, which was traditi- ally perceived as the only suitable reaction medium for the application of biocatalysts. The realization that most enzymes can function perfectly well under nearly anhydrous conditions and, in addition, display a number of useful properties, e. g., highly enhanced stability and different selectivity, has d- matically widened the scope of their application to the organic synthesis. Another great attraction of using organic solvents rather than water as a reaction solvent is the ability to perform synthetic transformations with re- tively inexpensive hydrolytic enzymes. It is worth reminding the reader that in vivo, the synthetic and hydrolytic pathways are catalyzed by different enzymes. However, elimination of water from the reaction mixture enables the reversal of hydrolytic enzymes and thus avoids the use of the expensive cofactors or activated substrates that are required for their synthetic count- parts."

Recenzje

"The handbook provides detailed descriptions of a variety of methods used for performing enzymatic reactions in nonaqueous media." - Journal of the American Chemical Society

"...includes detailed descriptions of the latest technologies used for biocatalysis in nearly anhydrous systems. Numerous specific enzymatic reactions, bioreactors, and useful techniques are carefully explained in a format intelligible to most readers in spite of the great diversity of the fields covered. This work of reference will be extremely valuable to those interested in enzymatic and asymmetric synthesis." - Natural Products Reports

Spis treści

Part I Control of Enzyme Activity in Nonaqueous Solvents Peter J. Halling Salt-Induced Activation of Enzymes in Organic Solvents: Optimizing the Lyophilization Time and Water Content Michael T. Ru, Jonathan S. Dordick, Jeffrey A. Reimer, and Douglas S. Clark Imprinting Enzymes for Use in Organic Media Joseph O. Rich and Jonathan S. Dordick Entrapment of Biocatalysts by Prepolymer Methods Atsuo Tanaka and Takamitsu Iida Microencapsulation of Enzymes and Cells for Nonaqueous Biotransformations Jeffrey A. Khan and Evgeny N. Vulfson Immobilization of Lipases on Hydrogels Abu Bakar Salleh, Norhaizan M. Esa, Mahiran Basri, Che Nyonya A. Razak, Wan Md Zin W. Yunus, and Mansor Ahmad Polyethylene Glycol-Modified Enzymes in Hydrophobic Media Ayako Matsushima, Yoh Kodera, Misao Hiroto, Hiroyuki Nishimura, and Yuji Inada Chemical Modification of Lipase for Use in Ester Synthesis Mahiran Basri, Kamaruzaman Ampon, Che Nyonya A. Razak, and Abu Bakar Salleh Preparation and Properties in Organic Solvents of Noncovalent PEG-Enzyme Complexes Francesco Secundo, Gianluca Ottlina, and Giacomo Carrea Preparations of a Lipid-Coated Enzyme and Activity for Reverse Hydrolysis Reactions in Homogeneous Organic Media Toshiaki Mori and Yoshio Okahata Very High Activity Biocatalysts for Low-Water Systems: Propanol-Rinsed Enzyme Preparations Barry D. Moore, Johann Partridge, and Peter J. Halling Methods for Measurement and Control of Water in Nonaqueous Biocatalysis George Bell, Peter J. Halling, Lindsey May, Barry D. Moore, Donald A. Robb, Rein Ulijn, and Rao H. Valivety Water Activity Control in Organic Media by Equilibration Through Membranes Ernst Wehtje and Patrick Adlercreutz Water Activity Control for Lipase-Catalyzed Reactions in Nonaqueous Media Joon Shick Rhee, Seok Joon Kwon, and Jeong Jun Han Immobilization of Enzymes and Control of Water Activity in Low-Water Media: Properties and Applications of Celite R-640 (Celite Rods) Lucia Gardossi Enzyme Activity and Enantioselectivity Measurements in Organic Media Amélie Ducret, Michael Trani, and Robert Lortie Calorimetric Methods in Evaluating Hydration and Solvation of Solid Proteins Immersed in Organic Solvents Mikhail Borisover, Vladimir Sirotkin, Dmitriy Zakharychev, and Boris Solomonov Detection of Structural Changes of Enzymes in Nonaqueous Media by Fluorescence and CD Spectroscopy Hideo Kise The Effects of Crown Ethers on the Activity of Enzymes in Organic Solvents Dirk-Jan van Unen, Johan F. J. Engbersen, and David N. Reinhoudt Control of Acid-Base Conditions in Low-Water Media Johann Partridge, Neil Harper, Barry D. Moore, and Peter J. Halling Enzymatic Acylation of _-Butylglucoside in Nonaqueous Media Marie-Pierre Bousquet, René-Marc Willemot, Pierre Monsan, and Emmanuel Boures Part II Synthetic Applications Herbert L. Holland Choosing Hydrolases for Enantioselective Reactions Involving Alcohols Using Empirical Rules Alexandra N. E. Weissfloch and Romas J. Kazlauskas Candida antarctica Lipase B: A Tool for the Preparation of Optically Pure Alcohols Didier Rotticci, Jenny Ottosson, Torbjörn Norin, and Karl Hult Enantioselective Lipase-Catalyzed Transesterifications in Organic Solvents Fritz Theil Pseudomonas cepacia Lipase-Catalyzed Enantioselective Acylation of 2-Substituted-1-alkanols in Organic Solvents Patrizia Ferraboschi and Enzo Santaniello Preparation of 2-, 3-, and 4-Methylcarboxylic Acids and the Corresponding Alcohols of High Enantiopurity by Lipase-Catalyzed Esterification Per Berglund and Erik Hedenström Optimization of Enzymatic

Blurb

In recent years, enzymatic catalysis in organic solvents-as opposed to aqueous solutions-has gained considerable attention as a powerful new approach to the preparation of natural products, pharmaceuticals, fine chemicals, and food ingredients. In Enzymes in Nonaqueous Solvents: Methods and Protocols, leading chemists, biochemists, biotechnologists, and process engineers summarize for the first time a wide range of methods for executing enzymatic transformations under nonaqueous conditions. Each method includes detailed step-by-step instructions for its successful completion, a list of materials, and ancillary notes that explain the scientific basis of the procedure, as well as troubleshooting. Also provided are a generic description of key reactions, advice on biocatalyst preparation, discussion of reaction conditions, and instructions on bioreactor design.
Comprehensive and state-of-the-art, Enzymes in Nonaqueous Solvents: Methods and Protocols offers today's synthetic chemists, biochemists, and process engineers all the essential information needed to carry out enzymatic reactions in nonaqueous media, as well as to successfully scale up to production quantities.