Synthesis of C-glycosyl amino acids by post- condensation modification of passerini products (CROSBI ID 709352)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa
Podaci o odgovornosti
Colić, Ivana ; Jerić, Ivanka
engleski
Synthesis of C-glycosyl amino acids by post- condensation modification of passerini products
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.
C-glycosil amino acids ; Passerini reaction ; multicomponent reaction
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
Podaci o prilogu
167-167.
2021.
objavljeno
Podaci o matičnoj publikaciji
European Symposium on Organic Chemistry : Book of abstracts & programme
Podaci o skupu
European Symposium on Organic Chemistry
poster
05.07.2021-06.07.2021
Gent, Belgija; online