carbohydrates chemistry
TRANSCRIPT
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CARBOHYDRATE CHEMISTRY
LOURDES L. BALCUEVA, M.D.
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CARBOHYDRATE CHEMISTRY
• Most abundant biomolecule in nature• Widely distributed in plants and animals• Main source of energy in humans;
oxidation of carbohydrates is the central energy-yielding pathway in most non-photo-synthetic cells
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Carbohydrate Chemistry
Other functions of CHO: - insoluble carbohydrate polymers serve as protective and structural elements in bacterial cell walls , plants, and connective tissues of animals - lubricate skeletal joints - attached to proteins, act as signals that determine intracellular location of glucoprotein
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CARBOHYDRATE CHEMISTRY
• - Carbohydrates are aldehyde or ketone derivative of polyhydric alcohol - General formula: Cn(H2O)n - Ex. Glucose: C6H12O6
- Glucose- most important carbohydrate; most dietary CHOs are absorbed in the circulation as glucose; - Glucose is the major metabolic fuel of mammals and fetuses.
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NOMENCLATURE
• 1. Monosaccharides- carbohydrate molecules with only one actual or potential sugar group; - cannot by hydrolyzed into simpler carbohydrates 2.Disaccharides- when 2 monosaccharides are combined together with release of water molecule; hydrolysis produces 2 monosaccharide units
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Carbohydrates
• 3. Oligosaccharides- condensation products of 2-10 monosaccharide units• 4. Polysaccharides- condensation products of more than 10 monosaccharides
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Monosaccharides
• - colorless, crystalline solids• - soluble in water but not in non-polar solvents - sweet taste - backbone is unbranched C chain; all carbon atoms are linked by single bonds - One C atom is double-bonded to an oxygen atom to form carbonyl grp.
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Aldose and ketose
• Aldose- if the carbonyl grp. is at the end of the carbon chain; monosaccharide is an aldehyde Ketose- if the carbonyl grp. is at any other position; monosacharide is a ketone
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Monosaccharides
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Structure of Glucose
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Haworth and Chair Form
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Monosacchides
• - monosaccharides with 5 or more carbon atoms in the backbone occur as cyclic structures in solution - carbonyl grp. forms covalent bond with oxygen of a hydroxyl grp along the chain
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Stereoisomers
• Stereoisomers-compounds having the same structural formula but differ in spatial
configuration - depends on the number of asymmetric C atom - formula: 2n where n is the number of asymmetric carbon atom - ex. Glucose: 2n is equal to 16
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Diastereo-isomers• Monosaccharides with the same molecular• Formula but differ in the configuration about 2
carbon atoms• Ex. Mannose and galactose
• Epimers- when sugars differ from one another only in configuration about one
carbon atom• Ex. Glucose and mannose; glucose and galactose
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Enantiomers
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D and L isomers
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Enantiomers
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Optical Activity
• - the ability of a solution to rotate the plane of plane-polarized light towards the right or
towards the left. - to the right or dextrorotatory: ( + ) - to the left or levorotatory: ( - ) -gives rise to 2 structures that are mirror image to each other called enantiomers
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Pyranose and Furanose RingStructure
• - results from general reaction between aldehydes and alcohols forming hemiacetals or between ketones and alcohols forming hemiketal - only aldoses with 5 or more carbon atoms can form pyranose rings - OH at C5 reacts with aldehyde grp at C1 - results in asymmetry at C1 resulting in a and B stereoisomers of D-glucose
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Pyranose and Furanose Structures
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a and B-stereoisomerism
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Glucose
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Glycosidic bond
• - monosacharides joined covalently by o-glycosidic bond
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Glycosidic Bond• Joins together 2 monosaccharides through a reaction
between the anomeric carbon of one unit and a hydroxyl group of another.
• Nomenclature: • - monosaccharide on the left: unit where the anomeric carbon is involved - O precedes the name of the first monosaccharide - a or B configuration of the first unit - furanosyl or pyranosyl - ( no. of C atom of first unit no. of C atom of 2nd unit)
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Disaccharides
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Disaccharides
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Disaccharides
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Polysaccharides
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Glycogen
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