Squaric Acid Diethylester: A Simple And Convenient Coupling Reagent

A new method for the covalent modification of polymers in a two-step process is described. Squaric acid diethylester reacts with primary or secondary aliphatic amines selectively to ester amides. It is shown for the first time that this class of compounds react with polymeric systems containing amin...

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Bibliographic Details
Published inZeitschrift für Naturforschung C. A journal of biosciences Vol. 46; no. 5; pp. 498 - 501
Main Authors Glüsenkamp, K.-H., Drosdziok, W., Eberle, G., Jähde, E., Rajewsky, M. F.
Format Journal Article
LanguageEnglish
Published Verlag der Zeitschrift für Naturforschung 01.06.1991
Subjects
Bifunctional Coupling Reagent
Covalent Modification
Squaric Acid Diamides
Squaric Acid Diethylester
Squaric Acid Monoamides
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Summary:A new method for the covalent modification of polymers in a two-step process is described. Squaric acid diethylester reacts with primary or secondary aliphatic amines selectively to ester amides. It is shown for the first time that this class of compounds react with polymeric systems containing amine functionalities (e.g. ε-amino groups of proteins) in aqueous solution, forming stable squaric acid diamide linkages. Three different monoamides were synthesized and the reaction rates of diamide formation versus hydrolysis were determined. Detailed kinetic studies revealed that unwanted hydrolytic side-reactions are more than ten times slower than the formation of squaric acid diamides
ISSN:0939-5075
1865-7125
DOI:10.1515/znc-1991-5-622