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Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment

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Abstract

An efficient three-step synthesis of a novel family of enantiomerically pure isocyanides derived from β3-isocyanopropionic acids was elaborated. Easily available N-formylated α-amino acids were used as starting materials towards this aim. The 3-step sequence (Arndt–Eistert reaction–Wolff rearrangement–dehydration) resulted in target isonitriles in good yields (up to 97%). As a result a new family of isocyanides bearing a fragment of β3-amino acids with different functional groups (amides, esters and short peptides) was obtained. It was demonstrated that these new isonitriles can be used in the Ugi and Passerini reactions to prepare short peptides and depsipeptides having a β-amino acid fragment incorporated.

Graphical abstract: Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment

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Publication details

The article was received on 26 Jun 2018, accepted on 31 Jul 2018 and first published on 31 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01507D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment

    D. P. Zarezin, O. I. Shmatova and V. G. Nenajdenko, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01507D

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