ISSN:
1434-4475
Keywords:
Crosslinking mechanism
;
N-Alkyl-1,4-dihydropyridines
;
N,N′-Alkyl-1,5-diiminopentanes
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The interaction of glutaraldehyde with model aliphatic amines was studied in order to understand the crosslinking reaction of glutaraldehyde with proteins. The reaction in organic solvents gave N-alkyl-1,4-dihydropyridines and N,N′-dialkyl-1,5-diiminopentanes. The isolated products are new or were previously described by us for the first time1. Hydration of the reaction products led to stable N-alkylpiperidines and N,N′-dialkyl-1,5-diaminopentanes. In aqueous solution the reaction depends on thepH: at apH above 7, N-alkyl-1,4-dihydropyridines and at apH below 7, polymers were obtained. For the crosslinking reaction of proteins with glutaraldehyde the following mechanism is proposed: Monomeric glutaraldehyde reacts with the protein to give intermediate N-alkyl-2,6-dihydroxypiperidines. Intramolecular dehydration leads to the corresponding N-alkyl-1,4-dihydropyridines. Condensation of the cyclic monohydrate of glutaraldehyde and N-alkyl-2,6-dihydroxypiperidines gives linear polymeric crosslinks containing α-oxo-N-alkylpiperidine units.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00904683
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