Organic 2 Review Problem 532

Organic 2 Review Problem 532 - S i6 PRACTICAL O RGANIC...

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Si6 PRACTICAL ORGANIC CHEMISTRY HOCH 1 C 4 H 4 O H \/ c- HO HOC HC :OH OH HC H O C 1 H 1 CH(CN)-O H HOC 1 H 4 O H V \/ CH 1 OH (I) of benzaldehyde. Arbutin (III) is a combination of glucose with hydro- quinone (i ,4-dihydroxy-benzene). Emulsin does not hydrolyse a-methylglucoside, whereas it readily hydrolyses P-methylglucoside, salicin, amygdalin and arbutin. This is an excellent ex- ample of the specificity of enzymes: C 1 H 11 O 6 -OCH, + H 1 O = C 6 H 11 O, + CH.OH {J-methyl-glucoside glucose C 6 H 11 O 8 -OC 6 H 4 CH 8 OH + H,O = C 6 H 11 O 6 + HOC 6 H 4 CH 1 OH salicin glucose salicyl alcohol Since an enzyme is a biological catalyst and therefore merely accelerates a reaction, it cannot alter the position of equilibrium in a reversible reaction. The hydrolysis of (J-methylglucoside is reversible and emulsin should therefore be capable also of synthesismg this compound from glucose and methanol. This synthesis can actually be carried out by the action of the enzyme on
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