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The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
Author(s) -
Hojnik Cornelia,
Müller Anne,
Gloe TobiasElias,
Lindhorst Thisbe K.,
Wrodnigg Tanja M.
Publication year - 2016
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.201600458
Subject(s) - amadori rearrangement , chemistry , glycoconjugate , glycosyl , conjugated system , carbohydrate , stereochemistry , substrate (aquarium) , combinatorial chemistry , scope (computer science) , organic chemistry , biochemistry , glycation , polymer , oceanography , receptor , computer science , programming language , geology
The Amadori rearrangement was investigated for the synthesis of C ‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C ‐glycosyl‐type glycoconjugates of the d ‐ gluco and d ‐ manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.