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Synthesis of a Carba-analog of S-Acetyl CoA,Acetonyldethio CoA.Synthesis of a Carba-analog ofS-Acetyl Coenzyme A,Acetonyl-dethio Coenzyme A; an Effective Inhibitor of Citrate Synthase

✍ Scribed by Stewart, Charles J. ;Wieland, Theodor

Publisher: Wiley (John Wiley & Sons)
Year: 1978
Weight: 514 KB
Volume: 1978
Category: Article
ISSN: 0074-4617
DOI: 10.1002/jlac.197819780107

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✦ Synopsis

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), K~i~ being 13.2 μmol/l.

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Synthesis of a carba-analog ofS-palmitoy

Synthesis of a carba-analog ofS-palmitoyl-coenzyme A, heptadecan-2-onyldethio-CoA, and ofS-Heptadecyl-CoA; effective inhibitors of citrate synthase and carnitine palmitoyltransferase

✍ Ciardelli, Thomas ;Stewart, Charles J. ;Seeliger, Annemarie ;Wieland, Theodor 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 English ⚖ 839 KB

## Abstract The syntheses of long chain alkyl‐coenzyme A derivatives**1** and**2** are reported. Heptadecan‐2‐onyldethio‐CoA**(1)** a carba analog of __S__‐palmitoyl‐CoA is obtained along with its 2′‐phosphate isomer**11** by the condensation of adenosine 2′,3′‐cyclic phosphate‐5′‐phosphoromorpholi