The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations. Issue 25 (27th June 2016)

• Record Type: Journal Article
• Authors: Hojnik, Cornelia; Müller, Anne; Gloe, Tobias‐Elias; Lindhorst, Thisbe K.; Wrodnigg, Tanja M.
• Is Part Of: European journal of organic chemistry. Issue 25(2016)
• Page Start: 4328
• Page End: 4337
• Publication Date: 2016-06-27
• Subjects: Rearrangement -- Glycoconjugates -- Carbohydrates -- Glycopeptides -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600458
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 thed ‐ gluco andd ‐ 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. Abstract : Amadori rearrangement employing (i) diamines, (ii) more complex amino‐functionalized glycosides, and (iii) amino acids, as amino components for the synthesis of C ‐glycosyl‐type neoglycoconjugates is described.