Cob(I)alamin reacts with sucralose to afford an alkylcobalamin: relevance to in vivo cobalamin and sucralose interaction.
Vitamin B(12), 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 B(12), 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 B(12) could occur in vivo.
Department of Materials and Environmental Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
Hitesh V
HV
Motwani
Shiran
S
Qiu
Bernard T
BT
Golding
Henrik
H
Kylin
Margareta
M
Törnqvist
D001711:Biotransformation; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D006801:Humans; D008099:Liver / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet; D013395:Sucrose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D053719:Tandem Mass Spectrometry; D014805:Vitamin B 12 / Q000737:chemistry / Q000494:pharmacology*
D013395:Sucrose; C026285:trichlorosucrose; D014805:Vitamin B 12