l35 - Oligomers Oligomers of bifunctional biomolecules. O...

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Unformatted text preview: Oligomers Oligomers of bifunctional biomolecules. O NH3 + O N H O + H 2O How many dipeptides can be constructed from the amino acids glycine and alanine? Use each one once. O NH3 + O N H O + H 2O amino acids O H3N R1 O + H3N R2 O O polypeptides O H3N R1 N H R2 O O amino acids O H3N glycine O polypeptides O H3N CH3 O O N H gly-ala O O H3N CH3 alanine O H3N CH3 N H O O ala-gly A1 B2 C3 D4 E5 F more than 5 How many disaccharides can be constructed from the carbohydrates glucose and galactose? OH + HO O + H2O How many disaccharides can be constructed from the carbohydrates glucose and galactose? OH + HO O + H2O carbohydrates H HO HO OH H O OH OH H H glucose H HO polysaccharides OH OH H H O HO OH H OH H O OH H OH H HO HO H carbohydrates OH H O OH OH H H glucose H HO polysaccharides OH OH H H O HO OH H OH H O OH H OH H O O H H OH OH OH OH H HO H OH OH O OH H HO H O OH H H O OH H O HO H OH H O OH OH H OH H H galactose OH H H galactose β H HO H A1 B2 C3 D4 E5 F more than 5 Lactose disaccharides cellobiose H H OH H OH CH 2O H O H H OH O H H OH CH 2OH O H H OH β−gl ucose Treatment of cellobiose with aqueous acid gives two moles of DDglucose. Using the curved arrow formalism show how this transformation is occuring transformation is occuring. cellobiose H CH 2OH O H H OH H H H OH CH 2OH O H H OH H H H OH OH OH H OH OH H H OH β−gl ucose OH H cellobiose synthetase H OH CH 2O H O H H OH H OH OH H OH H H OH H/H2O CH 2O H O H H OH cellobiose synthetase H OH O CH 2O H O H H OH H OH H O CH 2O H O H H OH OH H H/H2O H H OH CH 2O H O H H OH H OH H disaccharides disaccharides H H OH H OH H CH 2O H O H H OH H OH OH H H OH CH 2O H O H H OH O H H OH CH 2OH O H H OH OH H H H OH OH β−gl ucose OH H disaccharides H CH 2OH O H H OH H H H OH CH2 OH O H H H OH CH 2O H O H H OH H OH H H OH OH H H OH CH 2O H O H H OH O OH CH 2O H O H H OH OH β−gl ucose H OH H cellobiose CH 2O H O H H OH cellobiose OH H H OH CH 2O H H H O O H H H OH H OH H OH H OH CH2 OH O H OH H H OH CH2 OH OH O O H H H H OH H O n H OH H a polymer of polymer of glucose glucose β - linkages cellulose H OH CH 2 OH O H H OH H OH disaccharides disaccharides H maltose H O H CH 2OH O H H OH H H OH OH CH 2O H O H H OH OH H CH 2O H O H H OH OH β−gl ucose H H OH OH H CH 2 OH O H H OH H OH disaccharides H maltose H O H OH CH 2O H O H H OH OH H CH 2O H O H H OH OH β−gl ucose H H CH 2O H O H H OH H OH OH H CH 2O H H H O O H H OH H OH H H OH H H OH H OH OH H H H OH H OH CH 2O H O H H OH O OH H H OH CH 2O H O H H OH H OH H cellobiose OH H OH CH 2 OH O H H OH H OH disaccharides H maltose H O H OH CH 2O H O H H OH OH H CH 2O H O H H OH OH β−gl ucose H H OH OH H CH 2 OH O H H OH H OH H maltose H O H OH CH 2O H O H H OH OH H Would Would maltose be predicted to be predicted to be reduced reduced by NaBH4? NaBH4 H OH ? (A) yes (B) no H OH CH 2 OH O H H OH H OH H H nO H OH O CH 2 OH O HO H H OH H H CH 2 OH O H H OH H OH OH H another polymer of glucose α - linkages CH 2 OH O H H OH H OH H CH 2O H OH H H OH H OH OH H O O H starch Trehalose Trehalose is a disaccharide that can be obtained from fungi and algae. Choose the correct structure of trehalose based on the following information. CH O H 2 Carbohydrates readily polymerize to form oligomers and polymers. CH 2OH O H OH H H H OH H OH H OH H H OH CH 2OH O H H OH H O H H OH CH 2OH O H OH H H H H OH 1. Acid hydrolysis of trehalose yields only D-glucose. D2. Trehalose is hydrolyzed by α-glucosidase but not by β-glucosidase enzymes. 3. Trehalose does not react with NaBH4. 4. Methylation of trehalose followed by hydrolysis yields two of trehalose followed by hydrolysis yields two equivalents 2,3,4,6-tetra- methylequivalents of 2,3,4,6-tetra-O-methyl-D-glucose. H HO H OH O H H H OH H O HO OH OH H O OH H OH H H HO HO H OH H O OH O HO HH H O H H H OH H OH O H H OH OH α-D-glucose CHO H CH3O H H OH H OH H OH OCH3 H OCH3 OH CH2OCH3 H OH CH 2OH O H H OH OH β−gl ucose H H OH H H OH CH 2OH O H H OH O OH CH 2 OH O H H OH H O OH C H OH H HO HO H OH H O OH H A H OH H O OH H OH H H HO HO H OH H O HO OH H H O OH OH H O HO O H B D How many tetra saccharides are possible by attaching, using the glycosidic bond, a β-galactose to the following glucose tri saccharide saccharide? H OH OH β−gl ucose CH 2OH OH O OH H H OH H H H OH β−gal act ose H CH 2OH O H H OH H OH H H OH H OH CH 2OH O H H OH O H H H OH OH CH 2OH O H OH H H H CH 2OH O H H OH H OH O H H OH OH CH 2 OH O H H OH H O H H OH CH 2OH O H H OH OH H Many Many carbohydrate polymers are possible. CH 2OH O H OH H H H OH H OH H H C H2 OH O H H glu H OH OH H OH O H OH H CH2O H O H glu H OH H CH2OH O OH O H CH2O H O H glu H OH H OH H OH H OH H H OH CH 2OH O H H OH H O H H OH CH 2OH O H OH H H H H OH H OH CH 2OH O H H OH OH β−gl ucose H H OH H H OH CH 2OH O H H OH O OH CH 2 OH O H H OH H O OH Attach here A2 B3 C5 D6 E8 F 11 G 13 H 15 H gal H O H H OH g al act ose Many carbohydrate polymers are possible. Small polymeric carbohydrates play a very important role in cell recognition and communication. carbohydrates glu glu gal glu glu glu glu glu gal gal man glu man glu gal glu man glu gal glu glu What What are some common carbohydrate derivatives in biology? Amino sugars. H OH H HO HO H H O OH OH H What are some common carbohydrate derivatives in biology? Amino sugars. H OH H HO HO H H O OH NH2 H glucose glucosamine Oral glucosamine is commonly used for the treatment of used for the treatment of osteoarthritis. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage What are some common carbohydrate derivatives in biology? Amino sugars. H OH H HO HO H H O OH NH2 H What are some common carbohydrate derivatives in biology? Amino sugars. H OH H HO HO H H O OH NH2 H glucosamine structure! glucosamine H O HO CO 2 H O OH H H OH H O HO H H O O O NH H CH 3 Heparin is widely used as an injectable anticoagulant and has the highest negative charge density of any known biological molecule H H hyaluronic acid heparin Are glycolipids found in biology? Summary: What roles do carbohydrates play in biology? Many! H OH H HO HO H H OH H O OH glucose myelin sheath energy! neuron CH 2OH H H OH H OH OH O H H HO O H O OH H OH H OH sucrose H OH H OH CH2 OH O H H OH H H nO H OH H CH2 OH O HO OH H H O CH2 OH O H OH H H OH H galactocerbroside starch OH Summary: Summary: What roles do carbohydrates play in biology? glu glu gal glu Summary: What roles do carbohydrates play in biology? H OH H HO HO H H OH H O OH communication! H CH 2OH O H OH H H H H OH OH glucose structure! H H OH H OH CH 2OH O H H OH O CH 2OH O H H OH H O H H CH 2O H O H H OH H H H OH OH O CH 2OH O H OH H H OH H H OH H CH 2OH O H H OH H OH gal act ose O H H OH CH 2O H O H H OH OH O H n cellulose ...
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