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

Colić, Ivana; Bogović, Barbara; Jerić, Ivanka (2024) The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids. New Journal of Chemistry, 48 (28). pp. 12584-12590. ISSN 1144-0546

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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 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.

Item Type:	Article
Uncontrolled Keywords:	C-glycosyl α-amino acids; non-proteinogenic amino acids; oligomers; carbohydrates
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Neproteinogene aminokiseline za povećanje konformacijske raznolikosti peptida Ivanka Jerić IP-2022-10-9617 Znanstveno-istraživački projekt
Depositing User:	Lorena Palameta
Date Deposited:	14 Nov 2024 12:45
URI:	http://fulir.irb.hr/id/eprint/9295
DOI:	10.1039/d4nj02059f

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