دورية أكاديمية
أعرض في EDS

Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.

التفاصيل البيبلوغرافية
العنوان: Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.
المؤلفون: de Kleijne FFJ; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Ter Braak F; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Piperoudis D; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Moons PH; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Moons SJ; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Elferink H; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., White PB; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands., Boltje TJ; Institute for Molecules and Materials (IMM), Synthetic Organic Chemistry, Radboud University, 6525 AJ Nijmegen, The Netherlands.
المصدر: Journal of the American Chemical Society [J Am Chem Soc] 2023 Dec 06; Vol. 145 (48), pp. 26190-26201. Date of Electronic Publication: 2023 Nov 26.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 7503056 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5126 (Electronic) Linking ISSN: 00027863 NLM ISO Abbreviation: J Am Chem Soc Subsets: PubMed not MEDLINE; MEDLINE
أسماء مطبوعة: Publication: Washington, DC : American Chemical Society
Original Publication: Easton, Pa. [etc.]
مستخلص: The stereoselective introduction of glycosidic bonds (glycosylation) is one of the main challenges in the chemical synthesis of carbohydrates. Glycosylation reaction mechanisms are difficult to control because, in many cases, the exact reactive species driving product formation cannot be detected and the product outcome cannot be explained by the primary reaction intermediate observed. In these cases, reactions are expected to take place via other low-abundance reaction intermediates that are in rapid equilibrium with the primary reaction intermediate via a Curtin-Hammett scenario. Despite this principle being well-known in organic synthesis, mechanistic studies investigating this model in glycosylation reactions are complicated by the challenge of detecting the extremely short-lived reactive species responsible for product formation. Herein, we report the utilization of the chemical equilibrium between low-abundance reaction intermediates and the stable, readily observed α-glycosyl triflate intermediate in order to infer the structure of the former species by employing exchange NMR. Using this technique, we enabled the detection of reaction intermediates such as β-glycosyl triflates and glycosyl dioxanium ions. This demonstrates the power of exchange NMR to unravel reaction mechanisms as we aim to build a catalog of kinetic parameters, allowing for the understanding and eventual prediction of glycosylation reactions.
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تواريخ الأحداث: Date Created: 20231127 Latest Revision: 20231210
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC10704605
DOI: 10.1021/jacs.3c08709
PMID: 38008912
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-5126
DOI:10.1021/jacs.3c08709