Hydroxide-catalyzed isomerization of d-[1- 13C]mannose: Evidence for the involvement of 3,4-enediols

The KOH-catalyzed isomerization of d-[1- 13C]mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy. d-[1- 13C]Glucose and d-[1- 13C]fructose are generated during the reaction, as expected. In addition, however, [16- 13C]glucose, [6- 13C]mannose, and [6- 13C]fructose are produced...

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Veröffentlicht in:	Carbohydrate research 1986-10, Vol.154 (1), p.29-36
Hauptverfasser:	King-Morris, Melinda J., Serianni, Anthony S.
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbon Isotopes Chemical Phenomena Chemistry Exact sciences and technology Fructose Glucose Isomerism Labelled compounds chemistry Mannose Organic chemistry Reactivity and mechanisms
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Zusammenfassung:	The KOH-catalyzed isomerization of d-[1- 13C]mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy. d-[1- 13C]Glucose and d-[1- 13C]fructose are generated during the reaction, as expected. In addition, however, [16- 13C]glucose, [6- 13C]mannose, and [6- 13C]fructose are produced in small proportions, possibly via symmetrical 3,4-enediol intermediates. The involvement of the latter structures in 13C-label shifting is inferred from the observation of [1- 13C]sorbose and [6- 13C]sorbose in the reaction mixture.
ISSN:	0008-6215 1873-426X
DOI:	10.1016/S0008-6215(00)90019-3