Chapter_25 - P1 PCX JWDD052-25 JWDD052-Solomons-v3 Printer...

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P1: PCX Printer: Hamilton JWDD052-25 JWDD052-Solomons-v3 May 31, 2007 14:59 25 NUCLEIC ACIDS AND PROTEIN SYNTHESIS SOLUTIONS TO PROBLEMS 25.1 N N N N NH 2 H N N N N NH H N N N NH H and so on N N NN H 2 NH 2 Guanine: Adenine: Cytosine: N N N OH NH H H O N N N OH H and so on N N O H NH 2 and so on N N O H NH H N N OH NH Thymine (R = CH 3 ) or Uracil (R = H): H N N O H O R and so on N N OH N N O H OH OH R R H N H N H N H N H 574
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P1: PCX Printer: Hamilton JWDD052-25 JWDD052-Solomons-v3 May 31, 2007 14:59 NUCLEIC ACIDS AND PROTEIN SYNTHESIS 575 25.2 (a) The nucleosides have an N -glycosidic linkage that (like an O -glycosidic linkage) is rapidly hydrolyzed by aqueous acid but is one that is stable in aqueous base. (b) + H + + + + + - H OH HO N O Nucleoside OH H N O OH - H 2 O + H 2 O O H Heterocyclic base OH OH 2 O OH OH O + + + H + - H Deoxyribose H N HO HO HO OH OH H O HO HO 25.3 The reaction appears to take place through an S N 2 mechanism. Attack occurs preferentially at the primary 5 0 -carbon atom rather than at the secondary 3 0 -carbon atom. 25.4 C 6 H 5 C 6 H 5 C 6 H 5 O O NH O O EtO EtO O O O O Michael addition amide formation ( - EtOH) - EtOH + NH 2 O HN OEt
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Chapter_25 - P1 PCX JWDD052-25 JWDD052-Solomons-v3 Printer...

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