Stereospecific (methylenecyclopropyl)acetyl-CoA inactivation of general acyl-CoA dehydrogenase from pig kidney

Baldwin, John E.; Parker, David W.

doi:10.1021/jo00384a017

Cited by 32 publications

(44 citation statements)

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“…The alkyl methylenecyclopropane was again lithiated and then reacted with ethylene oxide. The resulting alcohol was oxidized with chromium trioxide [20]to yield the desired carboxylic acid. Proton NMR showed that the acids were not 100% pure, but, in view of the subsequent procedures to be used and the instability of the compounds, they were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Novel methylenecyclopropyl‐based acyl‐CoA dehydrogenase inhibitor

Broadway

Engel

1998

FEBS Letters

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A novel hexyl-substituted methylenecyclopropyl acetyl-CoA was tested as an enzyme-specific acyl-CoA dehydrogenase inhibitor. Its CoA ester generated in situ from the carboxylic acid and CoASH, displayed marked differences in inhibition specificity as compared to methylenecyclopropyl acetyl-CoA, consistent with the substrate specificities of the target enzymes. Thus methylenecyclopropyl acetyl-CoA inactivated short-chainspecific acyl-CoA dehydrogenase rapidly, medium-chain-specific acyl-CoA dehydrogenase much more slowly and had no effect on long-chain-or very long-chain-specific acyl-CoA dehydrogenases. The hexyl-substituent on the methylenecyclopropyl ring gave an inhibitor which rapidly inactivated MCAD and LCAD whilst VLCAD was inhibited more slowly and SCAD was essentially unaffected. In some cases (e.g. SCAD and MCPACoA) inhibition was accompanied by flavin bleaching. In other cases (e.g. LCAD and C T MCPA) less pronounced bleaching suggests a different chemistry of inhibition.z 1998 Federation of European Biochemical Societies.

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Section: Methodsmentioning

confidence: 99%

Novel methylenecyclopropyl‐based acyl‐CoA dehydrogenase inhibitor

Broadway

Engel

1998

FEBS Letters

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“…The solution was cooled in an ice bath and 50 pL of Jones reagent was added dropwise. 18 The mixture was stirred for 3 h; conversion to the acid was confirmed by TLC comparisons with a sample of unlabeled acid (Rf 0.2) using a 1 :1 ethyl acetate:5% ethanol-in-hexane mobile phase with anisaldehyde staining. using the same mobile phase and isolated from TLC scrapings by elution with 8 mL of ethyl acetate through a disposable pipette column.…”

Section: Discussionmentioning

confidence: 99%

“…The conversion of 2-14C in three steps to MCPA-CoA-14C (3-14C)was accomplished through a Jones oxidation, preparation of an active ester of (rnethylenecyclopropy1)acetic acid with N-hydroxysuccinimide, and reaction with coenzyme A, as detailed previously. 18 The product was thoroughly purified by HPLC and proved effective as an inactivator of GAD. The same chemistry with oxirane-l,2-13C2 as the source of label afforded 3-l3C2.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of carbon‐13 and carbon‐14 labeled (methylenecyclopropyl)acetyl‐CoA

Baldwin

Widdison

1990

Labelled Comp Radiopharmac

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“…Coma and death occur within 12 h in severe cases (Brown et al, 1992;Hassall & Hill, 1955;Hill, 1952). This illness is commonly known as Jamaican vomiting sickness (JVS) or more accurately toxic hypoglycaemic syndrome (THS) (Baldwin & Parker, 1987). It has been reported to affect young children more adversely than adults in a number of reported cases (Bressler et al, 1969;Brown et al, 1992;Hassall & Hill, 1955;Hill, 1952).…”

Section: Introductionmentioning

confidence: 99%

“…Although significant research has been conducted on the biochemistry of HG (Baldwin, Adlington, Bebbington, & Russell, 1994;Baldwin & Parker, 1987;Kean, 1974;Kean, 1989;Manchester, 1974;Ming-tain Lai, Eugene, & Hung-wen, 1991, 1993Tanaka, Isselbacher, & Shih, 1972;Tanaka et al, 1976), there has been no previous research that studied the HG exposure of Jamaican consumers. The goal of this study is to quantify the dietary exposure to ackee HG by Jamaican consumers.…”

Section: Introductionmentioning

confidence: 99%