Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Dedicated to Prof. Horst Kunz on the occasion of his 80th birthday

Abstract

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

Keywords

amino acid - cross-linker - desmosine - GOLD - biological activity - advanced glycation end-products

Publication History

Received: 16 November 2020

Accepted: 11 January 2021

Article published online:
22 February 2021

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