Current Industrial Production and Application of Saccharides in Japan

Published by: KRI, Inc.

Published: Dec. 26, 2001 - 202 Pages

Table of Contents

I. INTRODUCTION

II. GENERAL PRODUCTION METHODS

2.1 Extraction

2.2 Chemical Synthesis

2.2.1 Lactulose

2.2.2 Sugar Alcohols

2.3 Enzymatic Synthesis

2.3.1 Hydrolysis

2.3.2 Reverse Reaction

2.3.3 Transglycosylation

III. CARBOHYDRATE-ACTIVE ENZYMES UTILIZED IN THE MANUFACTURE OF SACCHARIDES

3.1 Enzymes Acting on Starch and Starch Saccharides

3.1.1 a-Amylase

3.1.2 b-Amylase

3.1.3 Glucoamylase

3.1.4 a-Glucosidase

3.1.5 Glucose-isomerizing Enzyme

3.1.6 Debranching Enzyme (Isoamylase, Pullulanase)

3.1.7 Cyclodextrin Glycosyltransferase

3.1.8 Branching Enzyme

3.1.9 Trehalose-Producing Enzymes

3.2 Enzymes Acting on Sucrose

3.2.1 b-Fructofuranosidase

3.2.2 a-Glucosyltransferase

3.3 Other Enzymes

3.3.1 Cellulase, b-Glucosidase

3.3.2 b-Galactosidase

3.3.3 a-Galactosidase

3.3.4 Xylanase

IV. PRODUCTION OF MONO- AND OLIGOSACCHARIDES

4.1 Saccharides Synthesized from Starch

4.1.1 Glucose

4.1.2 High Fructose Corn Syrup

4.1.3 Maltose

4.1.4 Maltotriose-Rich Maltooligosaccharide Mixture

4.1.5 Maltotetraose Syrup

4.1.6 Isomaltooligosaccharides

4.1.7 Nigerooligosaccharides

4.1.8 Gentiooligosaccharides

4.1.9 Cyclodextrin

4.1.10 Branched Cyclodextrin

4.1.11 Trehalose

4.1.12 Coupling Sugar

4.2 Saccharides Synthesized from Sucrose

4.2.1 Fructooligosaccharides

4.2.2 Lactosucrose

4.2.3 Palatinose and Trehalulose

4.2.4 Palatinose Oligosaccharides

4.3 Other Saccharides

4.3.1 Galactooligosaccharides

4.3.2 Raffinose

4.3.3 Soybean Oligosaccharides

4.3.4 Xylooligosaccharides

4.3.5 Chitin Oligosaccharides and Chitosan Oligosaccharides

4.3.6 Alginic Acid Oligosaccharides

4.3.7 Ascorbic Acid Glucoside

4.3.8 Glycosyl Stevioside

V. SACCHARIDES CURRENTLY UNDER DEVELOPMENT

5.1 Heterobranched Cyclodextrins

5.2 L-Arabinose

5.3 1,5-Anhydrofructose

5.4 Cycloamylose

5.5 Highly Branched Cyclic Dextrin

5.6 Agarooligosaccharides

5.7 Neoagarooligosaccharides

5.8 Ethyl a-Glucoside

5.9 Phosphoryl oligosaccharides

5.10 Others

VI. CURRENT TOPICS

6.1 From Newspapers

6.2 From the Annual Meeting of the Glycoscience and Related Sciences Society

6.3 Future Prospects

REFERENCES

FIGURES

2.1 Structure of Lactulos

2.2 Process Flow Sheet of Erythritole

2.3 Action of Glycosidase

2.4 Reaction System Used in the Column System Reaction

2.5 Time Course of Formation of Maltose and Isomaltose by Reverse Reaction of Glucose with Glucoamylase

2.6 Transglycosylation by Glycosidase

3.1 Reaction Points of Various Amylases on Starch

3.2 Schematic Representation of a Substrate Binding to the Active Site of TAA

3.3 Progressive Curves of Hydrolysis of Several Substrates by Saccharifying (left) and Liquefying (right) á -Amylase

3.4 Structures of á -Limit Dextrin of BLA

3.5 Hydrolysis Profiles of Two Glucoamylases on Soluble Starch and Maltose

3.6 Action Patterns of Pullulan-Hydrolyzing Enzymes

3.7 Thin Layer Chromatograms of Products Transferred to Various Acceptors by CGTase from B.macerans, B.circulans and B.stearothermophilus

3.8 HPLC Analysis of Products Transferred to D-Ribose and L-Rhamnose by CGTase from B.stearothermophilus, B.circulans, and B.macerans

4.1 Manufacturing Procedure of High Conversion Glucose Syrup

4.2 Liquefaction of Starch by Jet-Cooker

4.3 Manufacturing Procedure of Fine Powdered Glucose and Crystalline Dextrose

4.4 Manufacturing Procedure of High Fructose Corn Syrup

4.5 Structure of Maltose

4.6 Manufacturing Procedure of Maltose

4.7 Manufacturing Procedure of Maltooligomer Mix

4.8 Structure of Maltotetraose

4.9 Manufacturing Procedure of Maltotetraose

4.10 Saccharification Process by the Bioreactor System

4.11 Structures of Isomaltose and Panose

4.12 Manufacturing Procedure of Isomaltooligosaccharides

4.13 Effect of IMO-900 on Insoluble Glucan Synthesis

4.14 Structure of Nigerooligosaccharides

4.15 Manufacturing Procedure of Nigerooligosaccharides

4.16 Structure of Gentiooligosaccharides

4.17 Manufacturing Procedure of â -Glucooligosaccharides-Containing Syrups and Powder

4.18 Cyclodextrin Production by Various CGTases

4.19 Cyclodextrin Production Using a Reactor and UF Membrane Filter

4.20 Flow Diagram of the Production Process for ã -Cyclodextrin Using a Macrocyclic Complexing Agent

4.21 Production Process for Branched Cyclodextrins

4.22 Solubility of Cyclodextrins and Branched Cyclodextrins

4.23 Structure of Trehalose

4.24 Manufacturing Procedure of Trehalose

4.25 Chemical Structure of the Main Components of Coupling Sugar

4.26 Manufacturing Procedure of Coupling Sugar

4.27 Utilization of Sucrose

4.28 Structures of 1-Kestose and Nystose, Main Components of Fructooligosaccharides

4.29 Manufacturing Procedure of Fructooligosaccharides

4.30 Continuous Reaction System of Fructooligosaccharides with an Immobilized Enzyme

4.31 Changes in the Number of Bifidobacteria and pH in the Feces, and Consistency of Stool by the Administration of Fructooligosaccharides

4.32 Effect of Fructooligosaccharide Administration for Piglets on Their Growth

4.33 Structure of Lactosucrose

4.34 Time Course of Lactosucrose Production with â -Fructofuranosidase and Invertase-Deficient Yeast

4.35 Manufacturing Procedure of Lactosucrose

4.36 Effect of Lactosucrose Administration on Intestinal Microflora of Men

4.37 Production of Palatinose and Trehalulose from Sucrose

4.38 Manufacturing Process of Palatinose

4.39 Manufacturing Procedure of Palatinose

4.40 Structure of Palatinose Oligosaccharides

4.41 Structure of 4’-Galactosyllactose

4.42 Manufacturing Procedure of Galactooligosaccharides

4.43 Ratios of the Number of Bifidobacteria and Bacteroidaceae to Total Bacteria in Feces

4.44 Structure of Raffinose

4.45 Effect of Raffinose Administration on the Rat Intestinal Flora

4.46 Therapeutic Gain of Raffinose to Atopic Dermatitis

4.47 Structure of Soy Bean Oligosaccharides

4.48 Manufacturing Procedure of Soybean Oligosaccharides

4.49 Effect of SOB and SOE on Fecal â -Glucuronidase Activity of Volunteers

4.50 Effect of SOB and SOE on Fecal Azo-Reductase Activity of Volunteers

4.51 Structure of Xylooligosaccharides

4.52 The Xylan Column Reactor

4.53 Structure of Chitin- and Chitosan-Oligosaccharides

4.54 Alginic Acid Production with Hydrolysis of Alginate Lyase

4.55 Response of Barley Roots to A.L.L.

4.56 Inhibition Action of Pressure Increase by Sodium Alginate Oligosaccharides

4.57 Inhibition Action of Pressure Increase by Potassium Alginate Oligosaccharides

4.58 Structure of 2-O-á -Glucopyranosyl L-Ascorbic Acid

4.59 Stability of AA-2G in the Aqueous Solution at pH 7.0, 37°C

4.60 Structure of Stevioside

4.61 HPLC Analysis of SK-Sweet Z3 (A) and SK-Sweet (B)

5.1 Structure of Heterobranched Cyclodextrin

5.2 Hemolytic Effects of Branched CDs and Non-Branched CDs on Human Erythrocytes in 100 mM Isotonic Phosphate Buffer (pH 7.4)

5.3 Production of 1,5-AF from Starch and the Possible Structures of 1,5-AF in Water

5.4 Antioxidative Activities of 1,5-AF and Ascorbic Acid (VC)

5.5 Retrogradation of Cycloamylose

5.6 Crystal Structure of Cyclodextrin and Cycloamylose

5.7 Formation of Inclusion Compl

Abstract

In this report, the production of saccharides on an industrial scale is described.

The saccharides, or carbohydrates, are used in the form of polysaccharides, oligosaccharides, and monosaccharides. A typical development of the use of carbohydrates in Japan is oligosaccharides which are enzymatically produced using their hydrolysis, reverse reaction and transglycosylation. Nowadays, many oligosaccharides are industrially produced from starch, sucrose and lactose as raw materials. These oligosaccharides have functions such as formation of inclusion complex, low cariogenicity, anti-cariogenicity and bifidus growth factor. Current production of mono- and oligosaccharides is described.

Starch, sucrose and lactose, which are abundant in nature, are generally utilized as raw materials in the production of mono- and oligosaccharides for food processing. The enzymes utilized for the industrial production of saccharides are reviewed.

"Heterobranched cyclodextrins, L-arabinose, anhydrofructose, cycloamylose, highly branched cyclodextrins, agarooligosaccharides, and neoagarooligosaccharides are now under development. Production and properties of these saccharides are introduced. Recent topics on saccharides are also reviewed.

With increasing in the health consciousness of consumers, the future for products containing oligosaccharides seems to be greatly promising. These oligosaccharides may play an important role especially for the reduction of lifestyle-related diseases in the near future as well as the improvement of human health."

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