Issue 28, 2024

The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids

Abstract

C-Glycosyl amino acids are a group of C-glycosides in which a carbohydrate molecule is attached to the side chain or backbone of the amino acid via a C–C bond. Despite the numerous methods that have been developed for their synthesis, the C-glycosyl α-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids. The methodology is based on the modification of α-acyloxyamides obtained from the Passerini reaction using α-D-galactopyranose- and α-L-sorbofuranose-derived aldehydes as C-glycosyl donors. The protocol enabled the synthesis of homo- and heterochiral tetramers, and homo- and heterovalent tetramers in very good yields.

Graphical abstract: The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids

Supplementary files

Article information

Article type
Paper
Submitted
02 May 2024
Accepted
23 Jun 2024
First published
26 Jun 2024
This article is Open Access
Creative Commons BY-NC license

New J. Chem., 2024,48, 12584-12590

The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids

I. Colić, B. Bogović and I. Jerić, New J. Chem., 2024, 48, 12584 DOI: 10.1039/D4NJ02059F

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