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 › peer-review

8 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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title = "Characterization of acyl adenyl anhydrides: Differences in the hydrolytic rates of fatty acyl-AMP and aminoacyl-AMP derivatives",

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.",

author = "Schall, {Otto F.} and Iwao Suzuki and Murray, {Clare L.} and Gordon, {Jeffrey I.} and Gokel, {George W.}",

year = "1998",

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T1 - Characterization of acyl adenyl anhydrides

T2 - Differences in the hydrolytic rates of fatty acyl-AMP and aminoacyl-AMP derivatives

AU - Schall, Otto F.

AU - Suzuki, Iwao

AU - Murray, Clare L.

AU - Gordon, Jeffrey I.

AU - Gokel, George W.

PY - 1998/11/27

Y1 - 1998/11/27

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0031735593&partnerID=8YFLogxK

U2 - 10.1021/jo971874f

DO - 10.1021/jo971874f

M3 - Article

AN - SCOPUS:0031735593

VL - 63

SP - 8661

EP - 8667

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 24

ER -

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

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