Synthesis of novel glycopeptidomimetics via Nβ-protected-amino alkyl isonitrile based Ugi 4C reaction

C‐glycosides represent an important group of naturally occurring glycosylation derivatives but are also efficient mimetics of native O‐glycosides. Here, a one‐pot four‐component methodology is described toward a library of N‐alkylated C‐glycosyl amino acid derivatives comprising seven different isopropylidene‐protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X‐ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N‐alkylated C‐glycosyl amino acid derivatives as templates to access different biotic and abiotic secondary structures.

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N‐Alkylated C‐Glycosyl Amino Acid Derivatives: Synthesis by a One‐Pot Four‐Component Ugi Reaction

Vlahoviček-Kahlina

Štefanić

Vazdar

et al. 2020

ChemPlusChem

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Synthesis of N‐Glycosyl Conjugates through a Multicomponent Domino Process

Bellucci

Volonterio

2014

Eur J Org Chem

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The development of efficient methods for the combinatorial synthesis of N-glycosyl conjugates is vital for many fields of modern synthetic organic chemistry. Herein, we report a multicomponent domino process for the regioselective synthesis of a large array N-glycosyl-Asp-urea conjugates, which could be further functionalized in a chemoselective way, starting from easily accessible reactants such as N-glycosylamines, fumaric acid monoesters, azides, and isocyanates. The process occurs under very mild conditions, does not require the use of strong bases/acids or high temperature, and is highly versatile, working efficiently with a range of protecting groups and substituents

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Synthesis of 1, 5‐ Disubstituted Tetrazole via Ugi Azide Reaction: An Asymmetric Induction Approach

et al. 2017

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The Ugi‐azide reaction of an enantiopure amino acid derived isocyanides, amino acid esters, aldehydes and TMS‐N3 in MeOH:THF solvent system at 50 °C yielded peptidomimetics comprising tetrazole as amide bond isostere. Both N‐terminal (α‐isocyanoesters) and C‐terminal isocyanides (Nβ‐Cbz‐protected amino alkyl isocyanides) have been employed to yield diversified tetrazole peptidomimetics, having the possibility of further derivatization through either N‐ or C‐terminal chain elongation. Ugi‐azide reaction is a isocyanide based multi‐component reaction (IMCR), as a result, change in amino acid derived isocyanides had given structurally diverse products of biological interest. Good yields of products were obtained after column purification and were stable for shelf storage. The products are novel and were well characterized by Mass, 1H NMR and 13C NMR spectral studies. The present method offers several advantages such as one‐pot simple procedure, high yields and easy purification of products.

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Synthesis of novel glycopeptidomimetics via Nβ-protected-amino alkyl isonitrile based Ugi 4C reaction

Cited by 6 publications

References 37 publications

N‐Alkylated C‐Glycosyl Amino Acid Derivatives: Synthesis by a One‐Pot Four‐Component Ugi Reaction

N‐Alkylated C‐Glycosyl Amino Acid Derivatives: Synthesis by a One‐Pot Four‐Component Ugi Reaction

Synthesis of N‐Glycosyl Conjugates through a Multicomponent Domino Process

Synthesis of 1, 5‐ Disubstituted Tetrazole via Ugi Azide Reaction: An Asymmetric Induction Approach

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