General Properties of carbohydrates.pdf - 1.2 General...

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1.2General Properties,Occurrence, and Preparationof CarbohydratesJohn F. RobytLaboratory of Carbohydrate Chemistry and Enzymology, Departmentof Biochemistry, Biophysics, and Molecular Biology, 4252 Molecular BiologyBuilding, Iowa State University, Ames, IA 50011, USA[email protected]1General Properties and Occurrence of Carbohydrates. . . . . . . . . . . . . . . . . . . . . . .602Carbohydrate Property of Optical Rotation of Plane Polarized Light. . . . . . . .603The Structures of Carbohydrates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .613.1The Simplest Carbohydrates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .613.2Analogues ofD-Glyceraldehyde. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .623.3The Formation of Carbohydrates Containing More than Three Carbons. . . . . . . . . .623.4Special Properties of Pentoses and Hexoses. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .633.5D-Glucose: the Most Prominent Carbohydrate on the Earth. . . . . . . . . . . . . . . . . . . . . .643.6Occurrence ofD-Erythrose,D-Ribose, andD-Xylose. . . . . . . . . . . . . . . . . . . . . . . . . . . .663.7Occurrence of Hexoses. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .684Properties and Occurrence ofD-Glucose. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .684.1D-Glucose in the Free State. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .684.2D-Glucose in the Combined State. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .684.2.1Occurrence ofD-Glucose Combined withD-Fructose,D-Galactose,andD-Glucose, and High-EnergyD-Glucose Donors. . . . . . . . . . . . . . . . . . . . . . . . . . . .694.2.2Properties and Occurrence of Sucroseand Sucrose Oligosaccharides ContainingD-Galactose. . . . . . . . . . . . . . . . . . . . . . . . . .694.2.3Properties and Occurrence ofD-Glucose CombinedwithD-Galactose to Give Lactose and Higher Oligosaccharides. . . . . . . . . . . . . . . . . .714.2.4Properties and Occurrence ofα-D-GlucoseCombined withα-D-Glucose to Giveα,α-Trehalose. . . . . . . . . . . . . . . . . . . . . . . . . . . .725Properties and Occurrence ofD-Glucosein Polysaccharides and Cyclodextrins. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .725.1Properties and Occurrence of Starch. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .725.2Properties and Occurrence of Glycogen. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .745.3Properties and Occurrence of Dextrans, Alternan, Mutan, and Pullulan. . . . . . . . . . .745.4Properties and Occurrence ofD-Glucose in Cyclic Dextrins. . . . . . . . . . . . . . . . . . . . .755.5Properties and Occurrence of Cellulose. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .76In:Glycoscience. Fraser-Reid B, Tatsuta K, Thiem J (eds)Chapter-DOI 10-1007/978-3-540-30429-6_2: © Springer-Verlag Berlin Heidelberg 2008
581General Principles6Properties and Occurrence of Hemicelluloses. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .786.1Properties and Occurrence of Pectin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .797Cellulose-like Polysaccharides ContainingN-Acetyl-D-Glucosamine andD-Glucosamine. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .797.1Properties and Occurrence of Chitin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .797.2Properties and Occurrence of Chitosan. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .807.3Properties and Occurrence ofN-Acetyl-D-GlucosamineandN-Acetyl-D-Muramic Acid in Murein – The Bacterial Cell Wall. . . . . . . . . . . . . .807.4Properties and Occurrence of GlycosaminoglycansComposed of Amino Sugars and Uronic Acids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .817.4.1Hyaluronic Acid. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .817.4.2Chondroitin Sulfate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .817.4.3Dermatan Sulfate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .817.4.4Keratan Sulfate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .827.4.5Heparan Sulfate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .828Polysaccharides Containing Uronic Acids That Have Someof Their Carboxyl Groups Inverted by a C-5 Epimeraseto Give New Polysaccharides with New Properties. . . . . . . . . . . . . . . . . . . . . . . . . . .828.1Heparin Sulfate. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .828.2Alginates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .829Occurrence and Properties of Plant Exudate Polysaccharides. . . . . . . . . . . . . . . .8310Occurrence of Carbohydrates in Bacterial Polysaccharides. . . . . . . . . . . . . . . . . .8410.1Xanthan, a Water-Soluble Bacterial Polysaccharide. . . . . . . . . . . . . . . . . . . . . . . . . . . . .8410.2Pathogenic Bacterial Capsular Polysaccharides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .8511Properties and Occurrence ofD-Fructose in Polysaccharides. . . . . . . . . . . . . . . . .8612Properties and Occurrence of Sugar Alcohols. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .8612.1Glycerol. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .8612.2Properties and Occurrence of Free Sugar Alcohols,D-Glucitol,D-Mannitol, Ribitol, Xylitol, andD-Arabinitol. . . . . . . . . . . . . . . . . . . . . . .8612.3Sugar Alcohols in Teichoic Acids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .8713

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