Synthesis and interconversion of the four isomeric 6-oxo-2,4-heptadienoic acids

Journal Article · Tue Jan 01 04:00:00 EST 1985 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00204a004· OSTI ID:6720856

Feliu, A L; Seltzer, S

The synthesis of the structural isomers of 6-oxo-2,4-heptadienoic acid was undertaken as a means of providing analogues to investigate the structural requirements of maleylacetone cis-trans isomerase. 6-Oxo-2(Z),4(E)-heptadienoic acid and the methyl esters of 6-oxo-2(E),4(Z)-, 6-oxo-2(Z),4(Z)-, and 6-oxo-2(E),4(E)-heptadienoic acid were synthesized. Base-catalyzed hydrolysis of these esters furnished the corresponding acids except in the case of the 2Z,4Z isomer, which yielded instead the 2Z,4E acid. A mechanism for isomerization is suggested. Photocatalyzed isomerization of the acids and esters as a possible way of generating the ZZ acid was studied. The properties of the acids, their interaction with the enzyme, and what this suggests about the interaction of substrate maleylacetone with the enzyme is discussed. 16 references, 1 figure, 2 tables.

• Research Organization: Brookhaven National Lab., Upton, NY
• OSTI ID: 6720856
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:4; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400500 -- Photochemistry
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHEMISTRY
DATA
ESTERS
EXPERIMENTAL DATA
INFORMATION
ISOMERIZATION
KETO ACIDS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
PHOTOCHEMISTRY