Synthetic hydroxymethyl-porphyrins for protection of carboxy group

Autor:	Reiko Shibata, Hitoshi Tamiaki, Kouji Kumon
Rok vydání:	2007
Předmět:	chemistry.chemical_classification Carboxylic acid General Chemistry Porphyrin Thin-layer chromatography chemistry.chemical_compound chemistry polycyclic compounds Peptide synthesis Organic chemistry Phenyl group Moiety heterocyclic compounds Hydroxymethyl Methanol
Zdroj:	Journal of Porphyrins and Phthalocyanines. 11:434-441
ISSN:	1099-1409 1088-4246
DOI:	10.1142/s1088424607000497
Popis:	Hydroxymethyl-porphyrins were prepared by modifying tetraarylporphyrin possessing a p-(methoxycarbonyl)phenyl group at the meso-position and octaethylporphyrin. The synthetic alcohols reacted with carboxylic acids by the use of coupling reagents, to give the corresponding esters quantitatively. Due to the porphyrin dye moiety, the esterification was easily monitored on thin layer chromatography, and the resulting esters were highly soluble in most organic solvents and easily handled. The esters were readily cleaved by the action of an acid to give the original carboxylic acid and hydroxymethyl-porphyrin. Separation of the two species was performed by simple filtration: the carboxylic acid was soluble (filtrate) and the porphyrins were precipitates in methanol. These protective groups for carboxy groups were useful for peptide synthesis in the liquid phase.
Databáze:	OpenAIRE
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