Cyclodextrins are galnlng industrial interest owing to their particu lar structure. These cyclic amyloses are commonly composed of 6, 7 or 8 (named a-, 8-, y-CD) glucose units. They undergo complexation with quite a large number of substances by molecular inclusion. Their potential for in dustrial application is substantiated by their ability to protect fragile substances from oxygen and UV, to delay the evolution of volatiles and to aid the ancillary processing of dangerous or volatile substances in powder ed form. Though a-, 8- and y-CD exhibit different inclusion specificity, 8-CD has found…mehr
Cyclodextrins are galnlng industrial interest owing to their particu lar structure. These cyclic amyloses are commonly composed of 6, 7 or 8 (named a-, 8-, y-CD) glucose units. They undergo complexation with quite a large number of substances by molecular inclusion. Their potential for in dustrial application is substantiated by their ability to protect fragile substances from oxygen and UV, to delay the evolution of volatiles and to aid the ancillary processing of dangerous or volatile substances in powder ed form. Though a-, 8- and y-CD exhibit different inclusion specificity, 8-CD has found more attention than the others. This is due to the fact that most of the cyclodextrin producing enzymes known produce predominantly 8-CD. Fur thermore 8-CD is by far the least soluble form, leading to a relatively sim ple production and purification. Consequently 8-CD is already in production on an industrial scale [~] while a- and 8-CD are still more or less re garded as specialities. A further CD-producing enzyme has been found in the medium of K. pneu moniae [l], Since this CGT appeared to produce predominantly a-CD [~], it has been chosen to develop a process for the production of a-CD. MATERIALS AND METHODS Analysis of cyclodextrins: HPLC on Lichrosorb-NH . 10 ~m, with acetonitrile 2 water 65/35 per volume. Test for CGT activity: as described by Landert elsewhere in this Volume. Starch: potato starch as obtained from Blattmann, Wadenswil, Switzerland.
1. Chemistry and Production of Cyclodextrins.- 1.1. Cyclodextrin - A Paradigmatic Model.- 1.2. Cyclodextrin Research in Japan.- 1.3. Industrial Production of Cyclodextrins.- 1.4. Process Development for the Production of ?-Cyclodextrin.- 1.5.The Preparation and Some Properties of Glucosyl-Cyclodextrins.- 1.6. Separation of Cyclodextrins with Gelchromatography and HPLC.- 1.7. Rapid and Simple Spectrophotometric Method for Determination of Micro-Amounts of Cyclodextrins.- 2. Enzymology, Toxicology and Metabolism.- 2.1. Enzymology of the Cyclodextrins.- 2.2. A Photometric Test for the Cyclisation Activity of Cyclodextrin-Glycosyltransperases.- 2.3. Action of CGT on Beta Limit Dextrin of Amylopectin.- 2.4. Absorption and Metabolism of (?-Cyclodextrin by Rats.- 2.5. Toxicity Studies of Beta-Cyclodextrin.- 2.6. Absorption and Elimination of Cyclodextrin Derivatives by Rabbits and Rats.- 2.7. Renal Effects of Parenterally Administered Methylated Cyclodextrins on Rabbits.- 2.8. The Purification and Properties of Cyclodextrin Glycosyltransferase /CGT-ase/ of Bacillus Macerans (Abstract).- 2.9. A Rapid Method for Determination of CGT-ASE Activity (Abstract).- 2.10. Enzymatic Investigations with Cyclodextrins (Abstract).- 3. Cyclodextrin-Complexes.- 3.1. Structure Aspects of Cyclodextrin Inclusion Compounds.- 3.2. Structural Properties of Chemically Modified Cyclodextrins: The Crystal Structure of an Inclusion Complex Between Adamantanol and per-2,6-0-Methyl-?-Cyclodextrin.- 3.3. Application of a Stoichiometric Model of Cyclodextrin Complex Formation.- 3.4. The Complex Formation of Cyclodextrins and Related (1?4)-?-D-Glucans as Revealed by the Spin Labeling Techniques.- 3.5. A Simple Rule for Predicting Circular Dichroism Induced in Aromatic Guests by Cyclodextrin Hosts inInclusion Complexes.- 3.6. Transfer of Organic Molecules through Aqueous Layers Mediated by CD's and CD-Derivatives.- 3.7. Resolution of Chiral Sulfinyl Compounds Via ?-Cyclodextrin Inclusion Complexes.- 3.8. Interactions of ?-Cyclodextrin with Ionic Detergents.- 3.9. Thermofractography of Cyclodextrin-Complexes by Classical and Overpressured TLC Techniques.- 3.10. Thermoanalytical Investigations on Cyclodextrin Inclusion Compounds.- 3.11. Chiral Conformation of Bilirubin, Biliverdin and Benzil in Association with Cyclodextrin.- 3.12. Investigation of Cyclodextrin Complexes by X-Ray Powder Diffraction.- 3.13. Ternary Complexes of ?-Cyclodextrin and Benzoic Acid (Abstract).- 3.14. Polarographic Determination of Guest-Molecules in the Presence of ?-Cyclodextrin (Abstract).- 3.15. Hydrolysis of Phosphorochloridothionates in the Presence of ?-Cyclodextrin (Abstract).- 3.16. Molecular Dynamics of CD-Complexes in Solution: A 13C - N.M.R. Study.- 4. Cyclodextrin-Derivatives.- 4.1. The Chemistry of Cyclodextrin Derivatives.- 4.2. Cyclodextrin Derivatisation: Directed Reaction of Silylated Intermediates.- 4.3. Preparative Methods and NMR Analysis for Silylated Derivatives of Cyclodextrin.- 4.4. Cyclodextrin Polymers: Types and Specific Properties.- 4.5. Preliminary Studies on Tablet Disintegration by Sorption Calorimetry.- 4.6. Water-Soluble Cyclodextrin Polymers and Their Complexing Properties.- 4.7. Cyclodextrin Polymers as Specific Sorbents.- 4.8. Cyclodextrin-Crown Ether Combination (Abstract).- 5. Cyclodextrins in Pharmaceuticals.- 5.1. Cyclodextrin in Pharmaceutical Industry.- 5.2. A Forecast for Application of Cyclodextrins in the Pharma-Industry.- 5.3. Effects of Cyclodextrins on the Hemolysis Induced with Phenothiazine Neuroleptics.- 5.4. EnhancedBioavailability of Digitalis Glycoside by Cyclodextrin Complexation.- 5.5. Influencing Drug Absorption by ?-Cyclodextrin Complexation.- 5.6. Complex Equilibrium and Bioavailability.- 5.7. Menadione-?-Cyclodextrin Complex: Chemical Properties and Biological Effects.- 5.8. Stabilization of Camomile Oil with ?-Cyclodextrin.- 5.9. Pharmacological Effect of Lidocaine Dimethyl-?-Cyclodextrin Inclusion Complex.- 5.10. Investigations of Digitalis Glycosides and their Cyclodextrin Complexes (Abstract).- 5.11. Effect of Several Drugs and Their CD-Complexes on Heart-Rhythm of Blabera Craniifer (Abstract).- 5.12. Reduction of Indomethacin Side Effect with ?-Cyclodextrin in Gastro-Intestinal Tract (Abstract).- 5.13. Cyclodextrins and Congeners in Parenteral Applications.- 6. Application of Cyclodextrins in Foods Agriculture and Other Industries.- 6.1. Cyclodextrins in Foods, Cosmetics and Toiletries.- 6.2. Production and Application of ?-Cyclodextrin Complexes in the Food Industry.- 6.3. Stabilisation and Controlled Release of Perfume in Detergents.- 6.4. Separation of Phenylalanine and Tyrosine from Protein Hydrolysates.- 6.5. Effect of Cyclodextrin on Growth Processes and Productivity of Plants.- 6.6. Manifestation of Growth Control Effect of Cyclodextrin (CD) in Biosynthesis of DNA, RNA and Proteins in Germinating Barley.- 6.7. Biological Effects of the Cyclodextrin Complexes of 2-Chloroethylphosphonic Acid.- 6.8. Recovery of Solvent Vapours from Gaseous Phase by Cyclodextrin Solutions.- 6.9. Quality Control of the ?-Cyclodextrin Inclusion Complexes of Volatile Oils and Materials (Abstract).- Author Index.
1. Chemistry and Production of Cyclodextrins.- 1.1. Cyclodextrin - A Paradigmatic Model.- 1.2. Cyclodextrin Research in Japan.- 1.3. Industrial Production of Cyclodextrins.- 1.4. Process Development for the Production of ?-Cyclodextrin.- 1.5.The Preparation and Some Properties of Glucosyl-Cyclodextrins.- 1.6. Separation of Cyclodextrins with Gelchromatography and HPLC.- 1.7. Rapid and Simple Spectrophotometric Method for Determination of Micro-Amounts of Cyclodextrins.- 2. Enzymology, Toxicology and Metabolism.- 2.1. Enzymology of the Cyclodextrins.- 2.2. A Photometric Test for the Cyclisation Activity of Cyclodextrin-Glycosyltransperases.- 2.3. Action of CGT on Beta Limit Dextrin of Amylopectin.- 2.4. Absorption and Metabolism of (?-Cyclodextrin by Rats.- 2.5. Toxicity Studies of Beta-Cyclodextrin.- 2.6. Absorption and Elimination of Cyclodextrin Derivatives by Rabbits and Rats.- 2.7. Renal Effects of Parenterally Administered Methylated Cyclodextrins on Rabbits.- 2.8. The Purification and Properties of Cyclodextrin Glycosyltransferase /CGT-ase/ of Bacillus Macerans (Abstract).- 2.9. A Rapid Method for Determination of CGT-ASE Activity (Abstract).- 2.10. Enzymatic Investigations with Cyclodextrins (Abstract).- 3. Cyclodextrin-Complexes.- 3.1. Structure Aspects of Cyclodextrin Inclusion Compounds.- 3.2. Structural Properties of Chemically Modified Cyclodextrins: The Crystal Structure of an Inclusion Complex Between Adamantanol and per-2,6-0-Methyl-?-Cyclodextrin.- 3.3. Application of a Stoichiometric Model of Cyclodextrin Complex Formation.- 3.4. The Complex Formation of Cyclodextrins and Related (1?4)-?-D-Glucans as Revealed by the Spin Labeling Techniques.- 3.5. A Simple Rule for Predicting Circular Dichroism Induced in Aromatic Guests by Cyclodextrin Hosts inInclusion Complexes.- 3.6. Transfer of Organic Molecules through Aqueous Layers Mediated by CD's and CD-Derivatives.- 3.7. Resolution of Chiral Sulfinyl Compounds Via ?-Cyclodextrin Inclusion Complexes.- 3.8. Interactions of ?-Cyclodextrin with Ionic Detergents.- 3.9. Thermofractography of Cyclodextrin-Complexes by Classical and Overpressured TLC Techniques.- 3.10. Thermoanalytical Investigations on Cyclodextrin Inclusion Compounds.- 3.11. Chiral Conformation of Bilirubin, Biliverdin and Benzil in Association with Cyclodextrin.- 3.12. Investigation of Cyclodextrin Complexes by X-Ray Powder Diffraction.- 3.13. Ternary Complexes of ?-Cyclodextrin and Benzoic Acid (Abstract).- 3.14. Polarographic Determination of Guest-Molecules in the Presence of ?-Cyclodextrin (Abstract).- 3.15. Hydrolysis of Phosphorochloridothionates in the Presence of ?-Cyclodextrin (Abstract).- 3.16. Molecular Dynamics of CD-Complexes in Solution: A 13C - N.M.R. Study.- 4. Cyclodextrin-Derivatives.- 4.1. The Chemistry of Cyclodextrin Derivatives.- 4.2. Cyclodextrin Derivatisation: Directed Reaction of Silylated Intermediates.- 4.3. Preparative Methods and NMR Analysis for Silylated Derivatives of Cyclodextrin.- 4.4. Cyclodextrin Polymers: Types and Specific Properties.- 4.5. Preliminary Studies on Tablet Disintegration by Sorption Calorimetry.- 4.6. Water-Soluble Cyclodextrin Polymers and Their Complexing Properties.- 4.7. Cyclodextrin Polymers as Specific Sorbents.- 4.8. Cyclodextrin-Crown Ether Combination (Abstract).- 5. Cyclodextrins in Pharmaceuticals.- 5.1. Cyclodextrin in Pharmaceutical Industry.- 5.2. A Forecast for Application of Cyclodextrins in the Pharma-Industry.- 5.3. Effects of Cyclodextrins on the Hemolysis Induced with Phenothiazine Neuroleptics.- 5.4. EnhancedBioavailability of Digitalis Glycoside by Cyclodextrin Complexation.- 5.5. Influencing Drug Absorption by ?-Cyclodextrin Complexation.- 5.6. Complex Equilibrium and Bioavailability.- 5.7. Menadione-?-Cyclodextrin Complex: Chemical Properties and Biological Effects.- 5.8. Stabilization of Camomile Oil with ?-Cyclodextrin.- 5.9. Pharmacological Effect of Lidocaine Dimethyl-?-Cyclodextrin Inclusion Complex.- 5.10. Investigations of Digitalis Glycosides and their Cyclodextrin Complexes (Abstract).- 5.11. Effect of Several Drugs and Their CD-Complexes on Heart-Rhythm of Blabera Craniifer (Abstract).- 5.12. Reduction of Indomethacin Side Effect with ?-Cyclodextrin in Gastro-Intestinal Tract (Abstract).- 5.13. Cyclodextrins and Congeners in Parenteral Applications.- 6. Application of Cyclodextrins in Foods Agriculture and Other Industries.- 6.1. Cyclodextrins in Foods, Cosmetics and Toiletries.- 6.2. Production and Application of ?-Cyclodextrin Complexes in the Food Industry.- 6.3. Stabilisation and Controlled Release of Perfume in Detergents.- 6.4. Separation of Phenylalanine and Tyrosine from Protein Hydrolysates.- 6.5. Effect of Cyclodextrin on Growth Processes and Productivity of Plants.- 6.6. Manifestation of Growth Control Effect of Cyclodextrin (CD) in Biosynthesis of DNA, RNA and Proteins in Germinating Barley.- 6.7. Biological Effects of the Cyclodextrin Complexes of 2-Chloroethylphosphonic Acid.- 6.8. Recovery of Solvent Vapours from Gaseous Phase by Cyclodextrin Solutions.- 6.9. Quality Control of the ?-Cyclodextrin Inclusion Complexes of Volatile Oils and Materials (Abstract).- Author Index.
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