Enzymatic Reactions in Organic Media, 1996

The outlook of organic synthesis has changed many times during its tractable history. The initial focus on the synthesis of substances typical of living matter, exemplified by the first examples of organic chemistry through the synthesis of urea from inorganic substances by Liebig, was accepted as the birth of organic chemistry, and thus also of organic synthesis. Although the early developments in organic synthesis closely followed the pursuit of molecules typical in nature, towards the end of the 19th century, societal pressures placed higher demands on chemical methods appropriate for the emerging age of industrialization. This led to vast amounts of information being generated through the discovery of synthetic reactions, spectroscopic techniques and reaction mechanisms. The basic organic functional group transformations were discovered and improved during the early part of this century. Reaction mechanisms were elucidated at a growing pace, and extremely powerful spectroscopic tools, such as infrared, nuclear magnetic resonance and mass spectrometry were introduced as everyday tools for a practising organic chemist. By the 1950s, many practitioners were ready to agree that almost every molecule could be syn­ thesized. Some difficult stereochemical problems were exceptions; for example Woodward concluded that erythromycin was a "hopelessly complex target". This frustration led to a hectic phase of development of new and increasingly more ingenious protecting group strategies and functional group transformations, and also saw the emergence of asymmetric synthesis.

1 Enzymes in organic solvents: meeting the challenges.- References.- 2 Modes of using enzymes in organic media.- 2.1 Introduction.- 2.2 Choice of solvent.- 2.3 Effects of water.- 2.4 Solid enzyme preparations.- 2.5 Solubilized enzyme preparations.- 2.6 Other non-conventional reaction media.- 2.7 Comparisons between different modes of using enzymes in organic media.- References.- 3 Fundamentals of non-aqueous enzymology.- 3.1 Introduction.- 3.2 Structural integrity.- 3.3 Mechanistic integrity.- 3.4 Water.- 3.5 Solvent.- 3.6 Kinetics and thermodynamics of non-aqueous enzyme-catalyzed processes.- 3.7 Concluding remarks.- References.- 4 New enzymatic properties in organic media.- 4.1 Introduction.- 4.2 Specificity of enzymes in non-aqueous media.- 4.3 Thermal stability of enzymes in non-aqueous media.- 4.4 Conclusions.- References.- 5 Enzymatic resolutions of alcohols, esters, and nitrogen-containing compounds.- 5.1 Introduction.- 5.2 Quantitative aspects of enantioselective biocatalytic reactions.- 5.3 Stereochemical recognition of lipases.- 5.4 Working models for predicting stereoselectivity.- 5.5 Molecular and submolecular heterogeneity of Candida rugosa lipase.- 5.6 Sequential biocatalytic kinetic resolutions.- 5.7 Acyl donors and acceptors.- 5.8 Solvent and enzyme enantioselectivity.- 5.9 General behaviour of enzymes in organic solvents.- 5.10 Resolution of alcohols in organic solvents.- 5.11 Resolution of acids and esters in organic solvents.- 5.12 Lipase-mediated synthesis of nitrogen-containing compounds (amines, amides, amino acids, nitriles).- 5.13 Conclusion.- References.- 6 Regioselectivity of hydrolases in organic media.- 6.1 Introduction.- 6.2 Enzymatic acylation of polyhydroxylated compounds.- 6.3 Enzymatic hydrolysis of peracylated polyhydroxylated compounds.- 6.4 Scaled-up procedures.- 6.5 Closing remarks.- References.- 7 Hydrolase-catalysed asymmetric and other transformations of synthetic interest.- 7.1 Hydrolases.- 7.2 Lipases versus esterases: mechanistic models.- 7.3 Principles of enzymatic kinetic resolutions.- 7.4 Practical resolution of racemic mixtures: transesterification.- 7.5 Resolution of racemates without a chiral carbon centre and ferrocene-containing substrates.- 7.6 Hydrolases in other transformations.- References.- 8 Peptide synthesis.- 8.1 General aspects of protease-catalyzed peptide synthesis.- 8.2 Thermodynamically controlled synthesis.- 8.3 Kinetically controlled synthesis.- References.- 9 Productivity of enzymatic catalysis in non-aqueous media: New developments.- 9.1 Introduction.- 9.2 Enzymatic solvent-free synthesis.- 9.3 Enzymatic catalysis in eutectic mixtures.- 9.4 Design and implementation of continuous bioreactors.- 9.5 Conclusions.- References.- 10 Large-scale enzymatic conversions in non-aqueous media.- 10.1 Introduction.- 10.2 General aspects.- 10.3 Modification of oils and fats.- 10.4 Regioselective acylation of carbohydrates and steroids.- 10.5 Flavors and fragrances.- 10.6 Optically active pharmaceuticals and pesticides.- 10.7 Enzymatic polymer synthesis.- 10.8 Concluding remarks and future prospects.- References.- Epilogue: Prospects and challenges of biocatalysis in organic media.- References.

...it offers an excellent theoretical backgroind of, and access to, enzymology in organic solvents,...very useful for beginners, second owing to the detailed and comprehensive overview of applications, it can be used as a reference book. Trends in Food Science and Technology., a useful reference book - Food Manufacture