Hydrolysis of N-Alkyl Sulfamates and the Catalytic Efficiency of an S–N Cleaving Sulfamidase

…, R Wolfenden, DR Edwards

Index: Edwards, David R.; Lohman, Danielle C.; Wolfenden, Richard Journal of the American Chemical Society, 2012 , vol. 134, # 1 p. 525 - 531

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Citation Number: 2

Abstract

The final step in the degradation of heparin sulfate involves the enzymatic hydrolysis of its 2- sulfamido groups. To evaluate the power of the corresponding sulfamidases as catalysts, we examined the reaction of N-neopentyl sulfamate at elevated temperatures and found it to undergo specific acid catalyzed hydrolysis even at alkaline pH. A rate constant of 10–16 s–1 was calculated using the Eyring equation for water attack on the N-protonated species at ...