| DOI | Trouver le DOI : https://doi.org/10.1016/j.carres.2012.03.040 |
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| Auteur | Rechercher : Whitfield, Dennis M.1 |
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| Affiliation | - Conseil national de recherches du Canada. Thérapeutique en santé humaine
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| Format | Texte, Article |
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| Conférence | The XVI European Carbohydrate Congress, July 3-7, 2012, Sorrento, Italy |
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| Sujet | Glycosylation; Transition states; Density functional theory; Oxacarbenium ion |
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| Résumé | The Transition State (TS) for any chemical glycosylation reaction is not known with certainty. Both experimental and computational approaches have been limited due to the complexity of the problem. This work describes a preliminary computational ionization approach using density functional theory calculations to arrive at hypothetical TSs. The new TSs contain the glycosyl donor as anomeric triflates, the acceptor as methanol, some CH2Cl2 molecules, and a Li+ ion promoter. In this computational approach all glycosylations are disassociative in that the C-1–OTf bond length is greater then 2 Å before any nucleophilic attack. All nucleophilic attack requires some preassociation of the nucleophile with examples of the pre-attack complexation to donor oxygens. These hypothetical models are intended to guide both experimental and computational approaches to finding TSs for glycosylation reactions that can be used to optimize stereoselectivity of glycosylation. |
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| Date de publication | 2012-07-15 |
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| Dans | |
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| Langue | anglais |
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| Publications évaluées par des pairs | Oui |
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| Identificateur | S0008621512001486 |
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| Numéro NPARC | 21268686 |
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| Exporter la notice | Exporter en format RIS |
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| Signaler une correction | Signaler une correction (s'ouvre dans un nouvel onglet) |
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| Identificateur de l’enregistrement | 54b0da3d-6c71-45dc-9350-d23642e7fc91 |
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| Enregistrement créé | 2013-11-07 |
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| Enregistrement modifié | 2020-04-21 |
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