The role of sugar substituents in glycoside hydrolysis

MN Namchuk, JD McCarter, A Becalski…

Index: Namchuk, Mark N.; McCarter, John D.; Becalski, Adam; Andrews, Trevor; Withers, Stephen G. Journal of the American Chemical Society, 2000 , vol. 122, # 7 p. 1270 - 1277

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Citation Number: 130

Abstract

A series of monosubstituted deoxy and deoxyfluoro 2, 4-dinitrophenyl (DNP) β-d- glycopyranosides was synthesized and used to probe the mechanism of spontaneous β- glycoside hydrolysis. Their relative rates of hydrolysis followed the order 2-deoxy> 4-deoxy> 3-deoxy≈ 6-deoxy> parent> 6-deoxy-6-fluoro> 3-deoxy-3-fluoro> 4-deoxy-4-fluoro> 2- deoxy-2-fluoro. Hammett correlations of the pH-independent hydrolysis rates of each of ...