Characterization of acyl adenyl anhydrides: Differences in the hydrolytic rates of fatty acyl-AMP and aminoacyl-AMP derivatives

Otto F. Schall; Iwao Suzuki; Clare L. Murray; Jeffrey I. Gordon; George W. Gokel

doi:10.1021/jo971874f

Characterization of acyl adenyl anhydrides: Differences in the hydrolytic rates of fatty acyl-AMP and aminoacyl-AMP derivatives

Otto F. Schall, Iwao Suzuki, Clare L. Murray, Jeffrey I. Gordon, George W. Gokel

Research output: Contribution to journal › Article

7 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8661-8667
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	63
Issue number	24
DOIs	https://doi.org/10.1021/jo971874f
State	Published - Nov 27 1998

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Schall, O. F., Suzuki, I., Murray, C. L., Gordon, J. I., & Gokel, G. W. (1998). Characterization of acyl adenyl anhydrides: Differences in the hydrolytic rates of fatty acyl-AMP and aminoacyl-AMP derivatives. Journal of Organic Chemistry, 63(24), 8661-8667. https://doi.org/10.1021/jo971874f

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AU - Suzuki, Iwao

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AU - Gordon, Jeffrey I.

AU - Gokel, George W.

PY - 1998/11/27

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AB - 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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