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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
Author(s) -
Stewart Charles J.,
Wieland Theodor
Publication year - 1978
Publication title -
justus liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0075-4617
DOI - 10.1002/jlac.197819780107
Subject(s) - coenzyme a , chemistry , stereochemistry , acetyl coa , cofactor , citrate synthase , yield (engineering) , biochemistry , enzyme , reductase , materials science , metallurgy
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), K i being 13.2 μmol/l.