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Structure and Reactivity of Glycosyl Isocyanides
Author(s) -
Neochoritis Constantinos G.,
Ghonchepour Ehsan,
Miraki Maryam Kazemi,
ZarganesTzitzikas Tryfon,
Kurpiewska Katarzyna,
KalinowskaTłuścik Justyna,
Dömling Alexander
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801588
Subject(s) - isocyanide , chemistry , glycosyl , formamide , reactivity (psychology) , glycoconjugate , anomer , trisaccharide , nuclear magnetic resonance spectroscopy , stereochemistry , carbohydrate chemistry , combinatorial chemistry , organic chemistry , biochemistry , medicine , alternative medicine , pathology
3D structural information was obtained from mono‐, di‐ and trisaccharide formamide and isocyanide derivatives by analysis of their X‐ray crystal structure and NMR spectroscopy. The isocyanide anomeric effect was observed. Data mining of the Cambridge Structural Database (CSD) was performed and statistically confirmed our findings. Application of the glycoside isocyanides in the synthesis of novel glycoconjugates as drug‐like scaffolds by MCR chemistry underscores the usefulness of the novel building blocks.