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20-September-2008 09:29:06 - Monosaccharide Redirected from Monosaccharides Monosaccharides from Greek monos: single, sacchar: sugar are the simplest carbohydrates. They cannot be hydrolyzed into simpler sugars. They consist of one sugar and are usually colorless, water-soluble, crystalline solids. Some monosaccharides have a sweet taste. Examples of monosaccharides include glucose dextrose, fructose, galactose, xylose and ribose. Monosaccharides are the building blocks of disaccharides like sucrose common sugar and polysaccharides such as cellulose and starch. Further, each carbon atom that supports a hydroxyl group except for the first and last is chiral, giving rise to a number of isomeric forms all with the same chemical formula. For instance, galactose and glucose are both aldohexoses, but they have different chemical and physical properties. Contents 1 Structure 1.1 Cyclic structure 2 Monosaccharide nomenclature 2.1 Isomerism 3 List of monosaccharides 4 Reactions 5 See also 6 References 7 External links Structure α-D-Glucopyranose Haworth projection α-D-Glucopyranose Haworth projection β-D-GlucopyranoseHaworth projection β-D-GlucopyranoseHaworth projection With few exceptions e.g., deoxyribose, monosaccharides have the chemical formula CH2On + m with the chemical structure HCHOHnC=OCHOHmH. If n or m is zero, it is an aldehyde and is termed an aldose, otherwise it is a ketone and is termed a ketose. Monosaccharides contain either a ketone or aldehyde functional group, and hydroxyl groups on most or all of the non-carbonyl carbon atoms. Cyclic structure Most monosaccharides form cyclic structures, which predominate in aqueous solution, by forming hemiacetals or hemiketals depending on whether they are aldoses or ketoses between an alcohol and the carbonyl group of the same sugar. Glucose, for example, readily forms a hemiacetal linkage between its carbon-1 and the hydroxyl group of its carbon-5. Since such a reaction introduces an additional stereogenic center, two anomers are formed α-isomer and β-isomer from each distinct straight-chain monosaccharide. The interconversion between these two forms is called mutarotation.1 A common way of representing the cyclic structure of monosaccharides is the Haworth projection. In Haworth projection, the α-isomer has the OH- of the anomeric carbon under the ring structure, and the β-isomer, has the OH- of the anomeric carbon on top of the ring structure. In chair conformation, the α-isomer has the OH- of the anomeric carbon in an axial position, whereas the β-isomer has the OH- of the anomeric carbon in equatorial position. Monosaccharide nomenclature Monosaccharides are classified by the number of carbon atoms they contain: Triose, 3 carbon atoms Tetrose, 4 carbon atoms Pentose, 5 carbon atoms Hexose, 6 carbon atoms Heptose, 7 carbon atoms Octose, 8 carbon atoms Nonose, 9 carbon atoms Decose, 10 carbon atoms Monosaccharides are classified the type of carbonyl group they contain: Aldose, -CHO aldehyde Ketose, C=O ketone Isomerism The total number of possible stereoisomers of one compound n is dependent on the number of stereogenic centers c in the molecule. The upper limit for the number of possible stereoisomers is n = 2c. The only carbohydrate without an isomer is dihydroxyacetone or DHA. Monosaccharides are classified according to their molecular configuration at the chiral carbon furthest removed from the aldehyde or ketone group. The chirality at this carbon is compared to the chirality of carbon 2 on glyceraldehyde. If it is equivalent to D-glyceraldehyde's C2, the sugar is D; if it is equivalent to L-glyceraldehyde's C2, the sugar is L. Due to the chirality of the sugar molecules, an aqueous solution of a D or L saccharides will rotate light. D-glyceraldehyde causes polarized light to rotate clockwise dextrorotary; L-glyceraldehyde causes polarized light to rotate counterclockwise levorotary. Unlike glyceraldehyde, D/L designation on more complex sugars is not associated with their direction of light rotation. Since more complex sugars contain multiple chiral carbons, the direction of light rotation cannot be predicted by the chirality of the carbon that defines D/L nomenclature. D, configuration as in D-glyceraldehyde L, configuration as in L-glyceraldehyde All these classifications can be combined, resulting in names like D-aldohexose or ketotriose. List of monosaccharides This is a list of some common monosaccharides, not all are found in nature-some have been synthesized: Trioses: Aldotriose: glyceraldehyde Ketotriose: dihydroxyacetone Tetroses: Aldotetrose: erythrose and threose Ketotetrose: erythrulose Pentoses: Aldopentoses: arabinose, lyxose, ribose, deoxyribose, and xylose Ketopentoses: ribulose and xylulose Hexoses: Aldohexoses: allose, altrose, galactose, glucose, gulose, idose, mannose and talose Ketohexoses: fructose, psicose, sorbose and tagatose Heptoses: Keto-heptoses: mannoheptulose, sedoheptulose Octoses: octolose, 2-keto-3-deoxy-manno-octonate Nonoses: sialose Reactions Formation of acetals. Formation of hemiacetals and hemiketals. Formation of ketals. See also Look up Monosaccharide in Wiktionary, the free dictionary. Disaccharides Oligosaccharide Polysaccharides Sugar acid Sugar alcohol References ^ Pigman, Ward; Anet, E.F.L.J. 1972. Chapter 4: Mutarotations and Actions of Acids and Bases, in Pigman and Horton: The Carbohydrates: Chemistry and Biochemistry Vol 1A, 2nd ed., San Diego: Academic Press, 165-194. External links Nomenclature of Carbohydrates v d e Types of Carbohydrates General: Aldose | Ketose | Pyranose | Furanose Geometry Cyclohexane conformation | Anomer | Mutarotation Monosaccharides Trioses Ketotriose Dihydroxyacetone | Aldotriose Glyceraldehyde Tetroses Ketotetrose Erythrulose | Aldotetroses Erythrose, Threose Pentoses Ketopentose Ribulose, Xylulose Aldopentose Ribose, Arabinose, Xylose, Lyxose Deoxy sugar Deoxyribose Hexoses Ketohexose Psicose, Fructose, Sorbose, Tagatose Aldohexose Allose, Altrose, Glucose, Mannose, Gulose, Idose, Galactose, Talose Deoxy sugar Fucose, Fuculose, Rhamnose Heptose Sedoheptulose Multiple Disaccharides Sucrose | Lactose | Trehalose | Maltose Trisaccharides Raffinose | Melezitose | Maltotriose Tetrasaccharides Acarbose | Stachyose Other oligosaccharides Fructooligosaccharide FOS | Galacto-oligosaccharide GOS | Mannan-oligosaccharides MOS Polysaccharide Glycogen | Starch Amylose | Amylopectin | Cellulose | Chitin | Inulin | Dextrin | Glucan Beta-glucan Glycosaminoglycans Heparin | Chondroitin sulfate | Hyaluronan | Heparan sulfate | Dermatan sulfate | Keratan sulfate Aminoglycosides Kanamycin | Streptomycin | Tobramycin | Neomycin | Paromomycin | Apramycin | Gentamicin | Netilmicin | Amikacin Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Monosaccharide Categories: Monosaccharides Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية ÄŒesky Deutsch Eesti Ελληνικά Español Esperanto Ù?ارسی Français Hrvatski Ido Bahasa Indonesia Ã?slenska Italiano עברית Lietuvių МакедонÑ?ки Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий Shqip SlovenÄ?ina СрпÑ?ки / Srpski Basa Sunda Suomi Svenska ไทย Türkçe 粵語 ä¸æ–‡ This page was last modified on 5 August 2008, at 14:02
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