| The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates. | |
| | |
MedLine Citation:
|
PMID: 18346717 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate, 3,5-di-O-benzyl-alpha,beta-d-glucofuranose and further applied to d-glycero-d-gulo-heptose, which gave 'd-gluco-conjugates' in the alpha-anomeric form exclusively in high isolated yields. |
| | |
Authors:
|
Tanja M Wrodnigg; Christiane Kartusch; Carina Illaszewicz |
Related Documents
:
|
15575667 - Parallel supported synthesis of polyamine-imidazole conjugates. 6811507 - Microspectrofluorometric characterization of the fluorescent derivatives of biogenic am... 18841917 - Effects of substituents in the beta-position of 1,3-dicarbonyl compounds in bromodimeth... 3594727 - Nitroso transfer from alpha-nitrosamino aldehydes: implications for carcinogenesis. 21727987 - Synthesis of the proposed structure of phaeosphaeride a. 23037707 - One-step synthesis of 1-halo-1,3-butadienes via ruthenium-catalysed hydrohalogenative d... |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-03-02 |
Journal Detail:
|
Title: Carbohydrate research Volume: 343 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2008 Aug |
Date Detail:
|
Created Date: 2008-06-23 Completed Date: 2008-10-06 Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
|
Languages: eng Pagination: 2057-66 Citation Subset: IM |
Affiliation:
|
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria. t.wrodnigg@tugraz.at |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Glycoconjugates
/
chemical synthesis* |
| Chemical | |
Reg. No./Substance:
|
0/Glycoconjugates |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Cholecystokinin-33 is more effective than cholecystokinin-8 in inhibiting food intake and in stimula...
Next Document: Immobilization of glucoamylase by adsorption on carbon supports and its application for heterogeneou...