The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoco...
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Beilstein-Institut
2012-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.8.185 |
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doaj-b7c29bdf746d4e1ebe4dec15ff6016802021-02-02T06:44:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-09-01811619162910.3762/bjoc.8.1851860-5397-8-185The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugatesKatharina Gallas0Gerit Pototschnig1Florian Adanitsch2Arnold E. Stütz3Tanja M. Wrodnigg4Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, AustriaGlycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, AustriaGlycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, AustriaGlycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, AustriaGlycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, AustriaThe Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach.https://doi.org/10.3762/bjoc.8.185Amadori rearrangementC-glycosyl type glycoconjugatescarbohydrate elongationnon-natural carbohydrate conjugates |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Katharina Gallas Gerit Pototschnig Florian Adanitsch Arnold E. Stütz Tanja M. Wrodnigg |
| spellingShingle |
Katharina Gallas Gerit Pototschnig Florian Adanitsch Arnold E. Stütz Tanja M. Wrodnigg The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates Beilstein Journal of Organic Chemistry Amadori rearrangement C-glycosyl type glycoconjugates carbohydrate elongation non-natural carbohydrate conjugates |
| author_facet |
Katharina Gallas Gerit Pototschnig Florian Adanitsch Arnold E. Stütz Tanja M. Wrodnigg |
| author_sort |
Katharina Gallas |
| title |
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates |
| title_short |
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates |
| title_full |
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates |
| title_fullStr |
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates |
| title_full_unstemmed |
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates |
| title_sort |
amadori rearrangement as glycoconjugation method: synthesis of non-natural c-glycosyl type glycoconjugates |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2012-09-01 |
| description |
The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach. |
| topic |
Amadori rearrangement C-glycosyl type glycoconjugates carbohydrate elongation non-natural carbohydrate conjugates |
| url |
https://doi.org/10.3762/bjoc.8.185 |
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