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Synthesis of a Carba‐analog of S‐Acetyl CoA,Acetonyldethio CoA.Synthesis of a Carba‐analog of S‐Acetyl Coenzyme A,Acetonyl‐dethio Coenzyme A; an effective inhibitor of citrate synthase

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Wieland,  Theodor
Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Stewart, C. J., & Wieland, T. (1978). Synthesis of a Carba‐analog of S‐Acetyl CoA,Acetonyldethio CoA.Synthesis of a Carba‐analog of S‐Acetyl Coenzyme A,Acetonyl‐dethio Coenzyme A; an effective inhibitor of citrate synthase. Liebigs Annalen der Chemie, 1978(1), 57-65. doi:10.1002/jlac.197819780107.


Cite as: https://hdl.handle.net/21.11116/0000-0002-FDB7-3
Abstract
Acetonyldethio coenzyme A (1) together with its 2′‐phospho isomer 10 was obtained by the following reaction sequence: coupling of the glycol ketal 4 of 5‐amino‐2‐pentanone with N‐benzyloxycarbonyl‐β‐alanine, fusion of the deblocked aletheine analog 5 with the lactone of D‐2,4‐dihydroxy‐3,3‐dimethylbutyric acid to yield the pantetheine analog 6, which was phosphorylated at the 4′‐hydroxy group to form 7, and then condensation with adenosine 2′,3′‐cyclic phosphate 5′‐phosphoric morpholide. The isomeric mixture exhibited strong competitive inhibition of citrate synthase (S‐acetyl CoA + oxaloacetate), Ki being 13.2 μmol/l.