Synthesis of Cross-Linked Glycopeptides and Ureas by a Mechanochemical, Solvent-Free Reaction and Determination of Their Structural Properties by TEM and X-ray Crystallography

A highly efficient and cost‐effective green method for the synthesis of complex glycopeptides and ureas mediated by carbonyl diimidazole under solvent‐free conditions is reported. The reactions could be performed conveniently in a planetary ball mill by dry grinding, and the isolation of the novel s...

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Veröffentlicht in:ChemPlusChem (Weinheim, Germany) Germany), 2014-11, Vol.79 (11), p.1605-1613
Hauptverfasser: Kumar, Vajinder, Giri, Santosh Kumar, Venugopalan, Paloth, Kartha, K. P. Ravindranathan
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Sprache:eng
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Zusammenfassung:A highly efficient and cost‐effective green method for the synthesis of complex glycopeptides and ureas mediated by carbonyl diimidazole under solvent‐free conditions is reported. The reactions could be performed conveniently in a planetary ball mill by dry grinding, and the isolation of the novel sugar derivatives thus produced could be very efficiently achieved by size exclusion chromatography with environmentally benign substances. A diacetone galactose based diamide, upon crystallization, could be examined by X‐ray crystallography and was found to possess a heart‐shaped structure. Although the 4‐aminophenyl galactoside based diamide synthesized formed spherical particles, the alanine‐based diamide formed nanofilamentous/‐tubular structures as analyzed by TEM imaging. Just milling around! A highly efficient, cost‐effective, green method for the synthesis of complex glycopeptides and ureas mediated by N,N′‐carbonyldiimidazole under solvent‐free conditions is reported (see picture). The reactions are performed by dry grinding and isolation of the sugar derivatives is efficiently achieved by size exclusion chromatography with environmentally benign substances.
ISSN:2192-6506
2192-6506
DOI:10.1002/cplu.201402185