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

Colić, Ivana; Bogović, Barbara; Jerić, Ivanka (2024) The synthesis of oligomers containing alternating C-glycosyl a-amino acids and proteinogenic a-amino acids. New Journal of Chemistry, 48 . ISSN 1369-9261

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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 a-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating C-glycosyl a-amino acids and proteinogenic a-amino acids. The methodology is based on the modification of a-acyloxyamides obtained from the Passerini reaction using a-D-galactopyranose- and a-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.

Item Type:	Article
Uncontrolled Keywords:	C-glycosylation; C-glycosyl amino acids; peptides
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Increasing the conformational diversity of peptides with non-proteinogenic amino acids Ivanka Jerić IP-2022-10-9617 IP
Depositing User:	Ivanka Jerić
Date Deposited:	08 Jan 2026 08:22
URI:	http://fulir.irb.hr/id/eprint/10724
DOI:	10.1039/D4NJ02059F

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