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• W2029543249 startingPage "10371" @default.
• W2029543249 abstract "An investigation of the mechanism of solvolysis of CMP-N-acetyl neuraminate (CMP-NeuAc) is presented that includes synthesis of a family of isotopically labeled CMP-NeuAc's, use of new methodology for measurement of multiple kinetic isotope effects for acid-catalyzed solvolysis of CMP-NeuAc, and a stereochemical analysis of the reaction by solvolysis in aqueous methanol. The CMP-NeuAc isotopomers were synthesized with the following labels: [9-3H], [1-14C-N-acetyl], [2-14C], [1-14C], and [9-3H;3,3‘-2H] in yields of 78%, 86%, 76%, 85%, and 35%, respectively. The β-dideuterium kinetic isotope effect for solvolysis at pH 5.0, 37 °C, was 1.276 ± 0.008; the primary 14C isotope effect at C2, the anomeric carbon, was 1.030 ± 0.004; and an unusually large secondary 14C KIE was observed at C1, the carboxylate carbon, of 1.037 ± 0.004. Analysis of pH versus rate data and rate versus buffer concentration data establish that the solvolytic reaction is specific acid-catalyzed. Solvolysis of CMP-NeuAc at pH 5 or pH 6 in methanol/water mixtures afforded NeuAc, equal quantities of the α- and β-methyl glycosides of NeuAc, and small amounts of the elimination product 2,3-dehydro-N-acetyl neuraminic acid. The very large β-2H KIE, small primary 14C KIE, and the large secondary 14C KIE at the carboxylate carbon are consistent with a very late oxocarbenium ion-like transition state in which the carboxylate carbon is in a looser environment than in the ground state. The observation of racemization in the solvolysis reaction supports a reaction pathway that proceeds with the formation of a sialyl cation after the transition state." @default.
• W2029543249 created "2016-06-24" @default.
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• W2029543249 date "1996-01-01" @default.
• W2029543249 modified "2023-10-16" @default.
• W2029543249 title "Acid-Catalyzed Solvolysis of CMP-<i>N</i>-Acetyl Neuraminate: Evidence for a Sialyl Cation with a Finite Lifetime" @default.
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• W2029543249 doi "https://doi.org/10.1021/ja961811z" @default.
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