Acetyl coenzyme A synthetase catalyzed reactions of coenzyme A with α,β-unsaturated carboxylic acids

Smita S. Patel; David R. Walt

doi:10.1016/0003-2697(88)90642-2

Acetyl coenzyme A synthetase catalyzed reactions of coenzyme A with α,β-unsaturated carboxylic acids

Smita S. Patel, David R. Walt

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

α,β-Unsaturated coenzyme A (CoA) thioesters including acrylyl CoA, methacrylyl CoA, and propiolyl CoA were synthesized by catalysis with acetyl CoA synthetase (EC 6.2.1.1). After isolation from the enzymatic reactions, the products were found to be the result of 1,4 addition of CoASH to the double bond and addition of water to the triple bond of the initial acyl CoA adducts. Structural determinations of these products by ¹H NMR, ¹³C NMR, and the chemical reactions leading to their formation are described.

Original language	English (US)
Pages (from-to)	355-360
Number of pages	6
Journal	Analytical Biochemistry
Volume	170
Issue number	2
DOIs	https://doi.org/10.1016/0003-2697(88)90642-2
State	Published - May 1 1988
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biophysics
Biochemistry
Molecular Biology
Cell Biology

Keywords

C-13 NMR
acetyl CoA synthetase
acrylyl CoA
methacrylyl CoA
propiolyl CoA
proton NMR

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10.1016/0003-2697(88)90642-2

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title = "Acetyl coenzyme A synthetase catalyzed reactions of coenzyme A with α,β-unsaturated carboxylic acids",

abstract = "α,β-Unsaturated coenzyme A (CoA) thioesters including acrylyl CoA, methacrylyl CoA, and propiolyl CoA were synthesized by catalysis with acetyl CoA synthetase (EC 6.2.1.1). After isolation from the enzymatic reactions, the products were found to be the result of 1,4 addition of CoASH to the double bond and addition of water to the triple bond of the initial acyl CoA adducts. Structural determinations of these products by 1H NMR, 13C NMR, and the chemical reactions leading to their formation are described.",

keywords = "C-13 NMR, acetyl CoA synthetase, acrylyl CoA, methacrylyl CoA, propiolyl CoA, proton NMR",

author = "Patel, {Smita S.} and Walt, {David R.}",

note = "Funding Information: This work was supported by National Institutes of Health Grant GM 35329.",

year = "1988",

month = may,

day = "1",

doi = "10.1016/0003-2697(88)90642-2",

language = "English (US)",

volume = "170",

pages = "355--360",

journal = "Analytical Biochemistry",

issn = "0003-2697",

publisher = "Academic Press Inc.",

number = "2",

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TY - JOUR

T1 - Acetyl coenzyme A synthetase catalyzed reactions of coenzyme A with α,β-unsaturated carboxylic acids

AU - Patel, Smita S.

AU - Walt, David R.

N1 - Funding Information: This work was supported by National Institutes of Health Grant GM 35329.

PY - 1988/5/1

Y1 - 1988/5/1

N2 - α,β-Unsaturated coenzyme A (CoA) thioesters including acrylyl CoA, methacrylyl CoA, and propiolyl CoA were synthesized by catalysis with acetyl CoA synthetase (EC 6.2.1.1). After isolation from the enzymatic reactions, the products were found to be the result of 1,4 addition of CoASH to the double bond and addition of water to the triple bond of the initial acyl CoA adducts. Structural determinations of these products by 1H NMR, 13C NMR, and the chemical reactions leading to their formation are described.

AB - α,β-Unsaturated coenzyme A (CoA) thioesters including acrylyl CoA, methacrylyl CoA, and propiolyl CoA were synthesized by catalysis with acetyl CoA synthetase (EC 6.2.1.1). After isolation from the enzymatic reactions, the products were found to be the result of 1,4 addition of CoASH to the double bond and addition of water to the triple bond of the initial acyl CoA adducts. Structural determinations of these products by 1H NMR, 13C NMR, and the chemical reactions leading to their formation are described.

KW - C-13 NMR

KW - acetyl CoA synthetase

KW - acrylyl CoA

KW - methacrylyl CoA

KW - propiolyl CoA

KW - proton NMR

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EP - 360

JO - Analytical Biochemistry

JF - Analytical Biochemistry

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