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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Published on: August 20, 2018
Synthesis of d-glycopyranosyl depsipeptides using Passerini reaction
Banty Kumar1, Jyotirmoy Maity2, Bhawani Shankar3
1Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India; Department of Chemistry, Rajdhani College, University of Delhi, Delhi, 110015, India.
Abstract:
A protocol based on Passerini multi-component reaction has been developed for facile, efficient and atom economical synthesis of a small library of twenty potential bioactive (2R)-2-(d-glycopyranosyl)-2-acyloxyacetamides using perbenzylated d-glycopyranosyl aldehydes, substituted isocyanides and different aliphatic/aromatic carboxylic acids. All twenty synthesized d-glycopyranosyl α-acyloxy amides, commonly known as depsipeptides were unambiguously identified on the basis of their spectral (IR, 1H, 13C NMR, COSY, HSQC, NOESY and HRMS) data analysis.
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The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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