The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Cornelia Hojnik; Anne Mueller; Tobias Gloe; Thisbe Lindhorst; Tanja Wrodnigg

doi:10.1002/ejoc.201600458

The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Cornelia Hojnik, Anne Mueller, Tobias Gloe, Thisbe Lindhorst^*, Tanja Wrodnigg^*

^*Corresponding author for this work

Institute of Organic Chemistry (6410)

Research output: Contribution to journal › Article › peer-review

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 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.

Original language	English
Pages (from-to)	4328-4337
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201600458
Publication status	Published - 2016

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Human- & Biotechnology

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10.1002/ejoc.201600458Licence: CC BY 4.0

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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 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.",

author = "Cornelia Hojnik and Anne Mueller and Tobias Gloe and Thisbe Lindhorst and Tanja Wrodnigg",

year = "2016",

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AU - Gloe, Tobias

AU - Lindhorst, Thisbe

AU - Wrodnigg, Tanja

PY - 2016

Y1 - 2016

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AB - 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.

U2 - 10.1002/ejoc.201600458

DO - 10.1002/ejoc.201600458

M3 - Article

SN - 1099-0690

VL - 2016

SP - 4328

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Abstract

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