Enzymes in Nonaqueous Solvents Methods and Protocols 1st Edition by Evgeny Vulfson ISBN 978-1617372568 1617372560

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ISBN 10:  1617372560

ISBN 13: 978-1617372568

Author: Evgeny N. Vulfson

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.

Table of contents: 

PART I CONTROL OF ENZYME ACTIVITY IN NONAQUEOUS SOLVENTS

Peter J. Halling

1 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

2 Imprinting Enzymes for Use in Organic Media Joseph O. Rich and Jonathan S. Dordick

3 Entrapment of Biocatalysts by Prepolymer Methods Atsuo Tanaka and Takamitsu lida

4 Microencapsulation of Enzymes and Cells for Nonaqueous Biotransformations Jeffrey A. Khan and Evgeny N. Vulfson

5 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

6 Polyethylene Glycol-Modified Enzymes in Hydrophobic Media

Ayako Matsushima, Yoh Kodera, Misao Hiroto,

Hiroyuki Nishimura and Yuji Inada

7 Chemical Modification of Lipase for Use in Ester Synthesis Mahiran Basri, Kamaruzaman Ampon, Che Nyonya A. Razak, and Abu Bakar Salleh

8 Preparation and Properties in Organic Solvents of Noncovalent PEG-Enzyme Complexes Francesco Secundo, Gianluca Ottlina, and Giacomo Carrea

9 Preparation of a Lipid-Coated Enzyme and Activity for Reverse Hydrolysis Reactions in Homogeneous Organic Media Toshiaki Mori and Yoshio Okahata

10 Very High Activity Biocatalysts for Low-Water Systems:

Propanol-Rinsed Enzyme Preparations

Barry D. Moore, Johann Partridge, and Peter J. Halling

11 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.

12 Water Activity Control in Organic Media by Equilibration Through Membranes

Ernst Wehtje and Patrick Adlercreutz.

13 Water Activity Control for Lipase-Catalyzed Reactions in Nonaqueous Media

Joon Shick Rhee, Seok Joon Kwon, and Jeong Jun Han.

14 Immobilization of Enzymes and Control of Water Activity

in Low-Water Media: Properties and Applications of Celite R-640

(Celite Rods)

Lucia Gardossi.

15 Enzyme Activity and Enantioselectivity Measurements in Organic Media

Amélie Ducret, Michael Trani, and Robert Lortie

16 Calorimetric Methods in Evaluating Hydration and Solvation of Solid Proteins Immersed in Organic Solvents

Mikhail Borisover, Vladimir Sirotkin, Dmitriy Zakharychev, and Boris Solomonov

17 Detection of Structural Changes of Enzymes in Nonaqueous Media by Fluorescence and CD Spectroscopy

Hideo Kise….

18 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……

19 Control of Acid-Base Conditions in Low-Water Media

Johann Partridge, Neil Harper, Barry D. Moore, and Peter J. Halling….

20 Enzymatic Acylation of a-Butylglucoside in Nonaqueous Media

Marie-Pierre Bousquet, René-Marc Willemot, Pierre Monsan, and Emmanuel Boures

PART II SYNTHETIC APPLICATIONS

Herbert L. Holland…

21 Choosing Hydrolases for Enantioselective Reactions Involving Alcohols Using Empirical Rules

Alexandra N. E. Weissfloch and Romas J. Kazlauskas

22 Candida antarctica Lipase B: A Tool for the Preparation of Optically Active Alcohols Didier Rotticci, Jenny Ottosson, Torbjörn Norin, and Karl Hult

23 Enantioselective Lipase-Catalyzed Transesterifications in Organic Solvents Fritz Theil

24 Pseudomonas cepacia Lipase-Catalyzed Enantioselective Acylation of 2-Substituted-1-alkanols in Organic Solvents Patrizia Ferraboschi and Enzo Santaniello

25 Preparation of 2-, 3-, and 4-Methylcarboxylic Acids and the Corresponding Alcohols of High Enantiopurity by Lipase-Catalyzed Esterification Per Berglund and Erik Hedenström

26 Optimization of Enzymatic Enantiomeric Resolutions Through Solvent Selection Gianluca Ottlina, Francesco Secundo, Giorgio Colombo, and Giacomo Carrea

27 Chemoselective Amidification of Amino-Polyols Catalyzed with Lipases in Organic Solvents Thierry Maugard, Magali Remaud-Simeon, and Pierre Monsan…..

28 Synthesis of Esters Catalyzed by Lipases in Water-in-Oil Microemulsions Haralambos Stamatis, Aristotelis Xenakis, and Fragiskos N. Kolisis

29 Enzymatic Conversion of Organosilicon Compounds in Organic Solvents Takuo Kawamoto and Atsuo Tanaka

30 Synthetic Applications of Enzymes in Nonaqueous Media Valérie Rolland and René Lazaro

31 Enzymes in Nonaqueous Solvents: Applications in Carbohydrate and Peptide Preparation

Shui-Tein Chen, Boonyaras Sookkheo, Suree Phutrahul, and Kung-Tsung Wang….

32 Interface Bioreactor: Microbial Transformation Device on an Interface Between a Hydrophilic Carrier and a Hydrophobic Organic Solvent Shinobu Oda, Takeshi Sugai, and Hiromichi Ohta……

33 Yeast-Mediated Reactions in Organic Solvents Andrew J. Smallridge and Maurie A. Trewhella……

34 Biocatalysis in Pharmaceutical Process Development: SCH56592, a Case Study Brian Morgan, David R. Dodds, Michael J. Homann, Aleksey Zaks, and Robert Vail………..

PART III REACTION SYSTEMS AND BIOREACTOR DESIGN Evgeny N. Vulfson

35 Enzymatic Solid-to-Solid Peptide Synthesis Markus Erbeldinger, Uwe Eichhorn, Peter Kuhl, and Peter J. Halling

36 Enzymatic Synthesis and Hydrolysis Reactions of Acylglycerols in Solvent-Free Systems Cristina Otero, Jose A. Arcos, Hugo S. Garcia, and Charles G. Hill, Jr.

37 Solid-Gas Catalysis at Controlled Water Activity: Reactions at the Gas-Solid Interface Using Lipolytic Enzymes Sylvain Lamare and Marie Dominique Legoy

38 Solvent-Free Biotransformations of Lipids Tsuneo Yamane

39 Lipase-Catalyzed Synthesis of Sugar Fatty Acid Esters

in Supercritical Carbon Dioxide Haralambos Stamatis, Vasiliki Sereti, and Fragiskos N. Kolisis

40 Transformations in Frozen Aqueous Solutions Catalyzed by Hydrolytic Enzymes

Marion Haensler and Hans-Dieter Jakubke….

41 Enzymatic Synthesis of Sugar Fatty Acid Esters in Solvent-Free Media Douglas B. Sarney and Evgeny N. Vulfson…..

42 Biotransformations in Supersaturated Solutions David A. MacManus, Anna Millqvist-Fureby, and Evgeny N. Vulfson.

43 Enzymatic Transformations in Suspensions (I): One Solid Substrate and Product Volker Kasche and Antje Spieß

44 Biotransformations in Supercritical Fluids Nuno Fontes, M. Conceição Almeida, and Susana Barreiros……

45 Reverse Micellar Systems: General Methodology

Andrey V. Levashov and Natalia L. Klyachko

46 Enzymatic Transformations in Supercritical Fluids

Alain Marty and Jean-Stéphane Condoret

47 Enzymatic Transformations in Suspensions (II)

Adrie J. J. Straathof, Mike J. J. Litjens, and Joseph J. Heijnen

48 Characterization and Operation of a Micellar Membrane Bioreactor

Cristina M. L. Carvalho, Maria Raquel Aires-Barros, and Joaquim M. S. Cabral

49 Immobilization of Lipase Enzymes and Their Application in the Interesterification of Oils and Fats Alan D. Pellow and Maha M. A. Misbah

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