310-40 - CH 310 N LECTURE 40 Textbook Assignment: Chapter...

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CH 310 N LECTURE 40 Textbook Assignment: Chapter 25- Carbohydrates Homework (for credit): POW 13 (Due 5/2) Today’s Topics: Carbohydrates-Rxns; polymers XM3: Pick up in Chem Undrgrad Office Key posted Carbohydrates Carbohydrates Chapter 24
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N N - - Glycosides Glycosides • The anomeric carbon of a cyclic hemiacetal also undergoes reaction with the N-H group of an amine to form an N -glycoside glycoside N -glycosides of the purine and pyrimidine bases are structural units of nucleic acids N N N H N Purine N N Pyrimidine HN N H O O Uracil N N H O NH 2 Cytosine HN N H O O Thymine CH 3 N N Pyrimidine The Bases of Nucleic Acids The Bases of Nucleic Acids
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N N N H N N N N N H NH 2 HN N N N H O H 2 N Adenine Guanine Purine The Bases of Nucleic Acids The Bases of Nucleic Acids – the β - N -glycoside formed between D- ribofuranose and cytosine H H H H O HOCH 2 HO OH NH 2 O N N anomeric carbon a β - N -glycosidic bond 3’ 5’ N N - - Glycosides Glycosides
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Reduction to Reduction to Alditols Alditols • The carbonyl group of a monosaccharide can be reduced to an hydroxyl group by a variety of reducing agents, including NaBH 4 and H 2 /M (metal catalyst) OH OH HO HO CH 2 OH O CHO OH H H HO OH H CH 2 OH OH H NaBH 4 CH 2 OH OH H H HO OH H CH 2 OH OH H D-Glucitol (D-Sorbitol) D-Glucose β -D-Glucopyranose “Sugar alcohol” additive other alditols which are naturally occurring CH 2 OH CH 2 OH OH H OH H CH 2 OH CH 2 OH OH H H HO OH H CH 2 OH H HO H HO OH H CH 2 OH OH H D-Mannitol Xylitol Eryth rito l Used as “sugarless” sweetners
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Oxidation to Oxidation to Aldonic Aldonic Acids Acids • The -CHO group can be oxidized to -COOH O CH 2 OH HO HO OH OH C OH H H HO OH H CH 2 OH OH H O H C OH H H HO OH H CH 2 OH OH H O O - oxidizing agent D-Gluconate D-Glucose β - D-Glucopyranose ( β - D-Glucose) basic solution 2-Ketoses are oxidized to aldonic acids
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310-40 - CH 310 N LECTURE 40 Textbook Assignment: Chapter...

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