S-trifluoroacetonyl-coenzyme A:a 19F analogue of acetyl-coenzyme A.
S-Trifluoroacetonyl-coenzyme A has been synthesized in 87% yield by reaction of 1,1,1-trifluoro-3-bromopropanone with trilithium coenzyme A in presence of pyridine. The compound was characterized by its ultraviolet absorption spectrum and 1H and 19F nuclear magnetic resonance spectra. The alpha-methylene protons of the S-trifluoroacetonyl group exchanged with D2O and showed a pKa of 9.85 in S-trifluoroacetonylmercaptoethanol. S-Trifluoroacetonyl-coenzyme A is a competitive inhibitor of porcine heart citrate synthetase (Ki = 0.16 mM). It forms a binary complex with the enzyme and a ternary complex with enzyme/oxaloaetate binary complex, as evidenced ty the 19F shift. S-Trifluoracetonyl-coenzyme A and S-trifluoroacetonylmercaptoethanol form weak to moderately strong complexes with alpha-cyclodextrin and show little or no interaction with the methylglucose polysaccharide and lipopolysaccharides from Mycobacterium smegmatis [Smith, W. L., & Ballou, C. E. (1973) J. Biol. Chem. 248, 7118]. S-Trifluoroacetonylmercaptoethanol probably forms an inclusion complex with alpha-cyclodextrin because the interaction is reversed by compounds that do form inclusion complexes.
D000105:Acetyl Coenzyme A / Q000031:analogs & derivatives* / Q000378:metabolism; D002950:Citrate (si)-Synthase / Q000037:antagonists & inhibitors; D005461:Fluorine; D009682:Magnetic Resonance Spectroscopy; D008623:Mercaptoethanol / Q000031:analogs & derivatives; D008757:Methylglucosides / Q000378:metabolism; D009206:Myocardium / Q000201:enzymology; D011135:Polysaccharides, Bacterial / Q000378:metabolism; D011485:Protein Binding; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D008757:Methylglucosides; D011135:Polysaccharides, Bacterial; D005461:Fluorine; D008623:Mercaptoethanol; D000105:Acetyl Coenzyme A; D002950:Citrate (si)-Synthase