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- Glycosyl_donor abstract "A glycosyl donor is a carbohydrate mono- or oligosaccharide that will react with a suitable glycosyl acceptor to form a new glycosidic bond. By convention, the donor is the member of this pair that contains the resulting anomeric carbon of the new glycosidic bond. The resulting reaction is referred to as a glycosylation or chemical glycosylation.In a glycosyl donor, a leaving group is required at the anomeric position. The simplest leaving group is the OH group that is naturally present in monosaccharides, but it requires activation by acid catalysis in order to function as leaving group (in the Fischer glycosylation). More effective leaving groups are in general used in the glycosyl donors employed in chemical synthesis of glycosides. Typical leaving groups are halide, thioether, or imidate, but acetate, phosphate, and O-pentenyl are also employed. The natural glycosyl donors contain phosphate as leaving group. The so-called “armed-disarmed” principleThe concept of armed and disarmed glycosyl donors refers to the increased reactivity of benzylated over benzoylated glycosyl donors, a phenomenon observed very early, and which originates from the greater electron-withdrawing capability of ester blocking groups over ether blocking groups. However, it was Bertram Fraser-Reid who realised that benzylated glycosyl donors can be activated when benzoylated are not, and invented the terms armed glycosyl donor to the former and disarmed glycosyl donor to the latter. He and his group showed that armed glycosyl donors could be coupled onto a glycosyl acceptor, that at the same time was a disarmed glycosyl donor, without self-coupling of the disarmed donor/acceptor. This methodology allowed him to perform a one-pot synthesis of a trisaccharide via the O-pentenyl method.The concept has been extended to superarmed glycosyl donor by Mikael Bols and his collaborators. He realised that hydroxylic functional groups of carbohydrates are less electron-withdrawing toward the anomeric center when they are axial than equatorial, which means that glycosyl donor conformers with more axial oxy functions are more reactive. Protection of a glycosyl donor with bulky silyl groups (tert-butyldimethylsilyl or triisopropyl) cause it to change conformation to a more axial-rich conformation that, as a consequence, is more reactive, which Bols and his groups called superarmed. They showed that a superarmed donor can be coupled to an armed glycosyl donor/acceptor.".
- Glycosyl_donor wikiPageID "22484288".
- Glycosyl_donor wikiPageLength "3872".
- Glycosyl_donor wikiPageOutDegree "18".
- Glycosyl_donor wikiPageRevisionID "588852239".
- Glycosyl_donor wikiPageWikiLink Anomer.
- Glycosyl_donor wikiPageWikiLink Armed_and_disarmed_saccharides.
- Glycosyl_donor wikiPageWikiLink Bertram_Fraser-Reid.
- Glycosyl_donor wikiPageWikiLink Carbohydrate.
- Glycosyl_donor wikiPageWikiLink Carbohydrate_chemistry.
- Glycosyl_donor wikiPageWikiLink Category:Carbohydrate_chemistry.
- Glycosyl_donor wikiPageWikiLink Category:Organic_reactions.
- Glycosyl_donor wikiPageWikiLink Chemical_glycosylation.
- Glycosyl_donor wikiPageWikiLink Glycosidic_bond.
- Glycosyl_donor wikiPageWikiLink Glycosyl_acceptor.
- Glycosyl_donor wikiPageWikiLink Glycosyl_halide.
- Glycosyl_donor wikiPageWikiLink Glycosylation.
- Glycosyl_donor wikiPageWikiLink Koenigs–Knorr_reaction.
- Glycosyl_donor wikiPageWikiLink Leaving_group.
- Glycosyl_donor wikiPageWikiLink Mikael_Bols.
- Glycosyl_donor wikiPageWikiLink Oligosaccharide.
- Glycosyl_donor wikiPageWikiLink Silylation.
- Glycosyl_donor wikiPageWikiLink File:Glycosyl_donors_1.tif.
- Glycosyl_donor wikiPageWikiLinkText "Glycosyl donor".
- Glycosyl_donor wikiPageWikiLinkText "glycosyl donor".
- Glycosyl_donor hasPhotoCollection Glycosyl_donor.
- Glycosyl_donor wikiPageUsesTemplate Template:Reflist.
- Glycosyl_donor subject Category:Carbohydrate_chemistry.
- Glycosyl_donor subject Category:Organic_reactions.
- Glycosyl_donor hypernym Mono-.
- Glycosyl_donor type Carbohydrate.
- Glycosyl_donor type Reaction.
- Glycosyl_donor comment "A glycosyl donor is a carbohydrate mono- or oligosaccharide that will react with a suitable glycosyl acceptor to form a new glycosidic bond. By convention, the donor is the member of this pair that contains the resulting anomeric carbon of the new glycosidic bond. The resulting reaction is referred to as a glycosylation or chemical glycosylation.In a glycosyl donor, a leaving group is required at the anomeric position.".
- Glycosyl_donor label "Glycosyl donor".
- Glycosyl_donor sameAs m.05ztqkk.
- Glycosyl_donor sameAs Q17054443.
- Glycosyl_donor sameAs Q17054443.
- Glycosyl_donor wasDerivedFrom Glycosyl_donor?oldid=588852239.
- Glycosyl_donor isPrimaryTopicOf Glycosyl_donor.