Naslov
Synthesis of C-glycosyl amino acids by post- condensation modification of passerini products

Autori
Colić, Ivana ; Jerić, Ivanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
European Symposium on Organic Chemistry : Book of abstracts & programme / - , 2021, 167-167

Skup
European Symposium on Organic Chemistry

Mjesto i datum
Gent, Belgija; online, 05.07.2021. - 06.07.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Podatak o recenziji nije dostupan

Ključne riječi
C-glycosil amino acids ; Passerini reaction ; multicomponent reaction

Sažetak
C-Glycosides are a unique class of naturally occurring compounds with a diverse array of biological properties. Because C-glycosides are metabolically more stable compared to their O- or N- counterparts, they are widely utilized in biomedical and drug discovery studies of glycopeptides and proteins. C-glycosyl amino acids represent a special group of C-glycosides. The interest in the synthesis of these compounds originates from their subsequent incorporation into peptides.2 Oligomers composed of such non- natural amino acids represent highly valuable tools not just in medicinal chemistry but also in material science (self-assembly, formation of different types of nanostructures, etc). Routes developed for the synthesis of C-glycosyl amino acids, installation of an amino acid moiety onto a glycosyl framework rely on the use of well- established α-amino acid synthesis strategies, such as robust, stereoselective, multicomponent approach with sugar derivatives.2, 3 We utilized a three-component Passerini reaction to convert carbonyl compounds to α-acyloxyamides. Passerini products were synthesized using three different isopropylidene-protected aldehydes (sorbose, galactose, and allose derivative) as carbonyl components, amino acid-derived isocyanides (L and D), and acetic acid, in high yields and diastereoselectivities.4 Hydrolysis of Passerini products under basic conditions afforded α-hydroxy C-glycosyl derivatives. Further transformations aimed to transform OH to NH2 group afforded dipeptides comprising C-glycosyl amino acid (Figure 1). Such monomers will be used in the synthesis of homo- and heterochiral oligomers.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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