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Cob(I)alamin Reacts with Sucralose to Afford an Alkylcobalamin: Relevance to In Vivo Cobalamin and Sucralose Interaction
Department of Materials and Environmental Chemistry, Stockholm Unviersity, Stockholm 106 91 , Sweden.
Department of Material and Environmental Chemistry, Stockholm University, Stockholm 106 91, Sweden.
School of Chemistry, Newcastle University, United Kingdom.
Norwegian Institute for Air Research, Polar Environmental Centre, Norway.ORCID iD: 0000-0002-5972-1852
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2011 (English)In: Food and Chemical Toxicology, ISSN 0278-6915, E-ISSN 1873-6351, Vol. 49, no 4, 750-757 p.Article in journal (Refereed) Published
Abstract [en]

Vitamin B12, viz., cyano- or hydroxo-cobalamin, can be chemically or enzymatically converted into the derivatives methyl- and adenosyl-cobalamin, which are complex organometallic cofactors associated with several cobalamin-dependent enzymes. The reduced form of vitamin B12, cob(I)alamin {Cbl(I)}, obtained by reduction of hydroxocobalamin (OH-Cbl) with e.g. sodium borohydride, is one of the most powerful nucleophiles known. Cbl(I) was shown to react readily with the synthetic sweetener sucralose (1,6-dichloro-1,6-dideoxy-β-d-fructofuranosyl-4-chloro-4-deoxy-α-d-galactopyranoside) in an aqueous system to form an alkylcobalamin (Suc-Cbl). This occurred by replacement of one of the three chlorine atoms of sucralose with a cobalamin moiety. The efficiency of trapping sucralose in presence of excess Cbl(I) was estimated to be >90%. Furthermore, in an in vitro study using human liver S9 with NADPH regeneration, in presence of OH-Cbl and sucralose, Suc-Cbl was shown to be formed. The Suc-Cbl was characterized primarily by LC-ESI+-MS/MS. Given the human consumption of sucralose from food and beverages, such a reaction between the sweetener and reduced vitamin B12 could occur in vivo.

Place, publisher, year, edition, pages
Springer, 2011. Vol. 49, no 4, 750-757 p.
Keyword [en]
Hydroxocobalamin, sucralose, sodium borohydride, NADPH, alkylcobalamin, LC-MS/MS
National Category
Environmental Sciences Analytical Chemistry Environmental Health and Occupational Health Pharmacology and Toxicology
Identifiers
URN: urn:nbn:se:liu:diva-68261DOI: 10.1016/j.fct.2010.11.037ISI: 000289136100006PubMedID: 21130828OAI: oai:DiVA.org:liu-68261DiVA: diva2:417146
Available from: 2012-01-13 Created: 2011-05-16 Last updated: 2017-12-11Bibliographically approved

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Kylin, Henrik

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