Characterization of Acyl Adenyl Anhydrides:  Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives

An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl g...

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Veröffentlicht in:Journal of organic chemistry 1998-11, Vol.63 (24), p.8661-8667
Hauptverfasser: Schall, Otto F, Suzuki, Iwao, Murray, Clare L, Gordon, Jeffrey I, Gokel, George W
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container_end_page 8667
container_issue 24
container_start_page 8661
container_title Journal of organic chemistry
container_volume 63
creator Schall, Otto F
Suzuki, Iwao
Murray, Clare L
Gordon, Jeffrey I
Gokel, George W
description An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue.
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title Characterization of Acyl Adenyl Anhydrides:  Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives
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