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Synthesis of a Deoxo Analog of (3 S )‐Citryl‐CoA: (3 R )‐3,4‐Dicarboxy‐3‐hydroxybutyl‐CoA
Author(s) -
Eggerer Hermann,
Giesemann Walter,
Aigner Horst
Publication year - 1983
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198319830911
Subject(s) - chemistry , yield (engineering) , thioester , coenzyme a , bromide , tricarboxylic acid , hydrolysis , acetyl coa , citric acid cycle , derivative (finance) , enzyme , stereochemistry , medicinal chemistry , organic chemistry , materials science , economics , financial economics , reductase , metallurgy
The citryl thioester 1 was reduced in mmol scale with sodium tetrahydroborate to yield 2‐hydroxy‐2‐(2‐hydroxyethyl)butanedioic acid ( 2 ) in 70% yield. The acid was converted into the dimethyl ester 3 and further to the 2‐(2‐bromoethyl) derivative 4 . This bromide was used to prepare the title compound 7 by reaction with coenzyme A, either directly, or by hydrolysis of the isolated dimethyl ester 6 . The kinetic and X‐ray crystallographic results obtained with 7 and the enzyme citrate synthase of the tricarboxylic acid cycle are discussed.