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• W2034763810 abstract "Potentiometric titration of five α-alkylcobalamins, in which the axial organic ligand is in the ‘lower’ (α) axial position preventing coordination of the axial nucleotide, has provided the first values of the pKa of the conjugate acid of the pendent, but uncoordinated, benzimidazole nucleotide in cobalamins. In every case, these values are lower than the pKa of the conjugate acid-of the free nucleoside, α-ribazole, at the same temperature. This suggests that, as is the case with base-off dicyanocobalamin and base-off but benzimidazole deprotonated β- alkylcobalamins, the free base nucleotide in the α-alkylcobalamins is associated with a corrin ring side chain to form what is known as the ‘tuck-in’ species. The data permit calculation of apparent equilibrium constants for formation of the ‘tuck-in’ species of the α-alkylcobalamins which vary from about 0.3 to 1.3, but are essentially temperature independent for a given complex. The isoenthalpic nature of this equilibrium is consistent with the principle interaction in the ‘tuck-in’ species being a hydrogen bond between the nucleotide B3 nitrogen and a side chain amide N-H, as is the case for dicyanocobalamin and the base-off β-alkylcobalamins. Further evidence for formation of ‘tuck-in’ species in α-alkylcobalamins has been obtained from comparison of the 13C NMR resonances of the pendent nucleotide of these complexes with those of the free nucleotide, α-ribazole-3′-phosphate, and with those of dicyanocobalamin, in which the ‘tuck-in’ species is well characterized. These spectral comparisons suggest that formation of the ‘tuck-in’ species may be accompanied by a change in conformation about the nucleotide N-glycosidic bond, and that the conformation of the nucleotide ribose moiety in the ‘tuck-in’ species of the α-alkylcobalamins may be different from that in dicyanocobalamin." @default.
• W2034763810 created "2016-06-24" @default.
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• W2034763810 date "1992-07-01" @default.
• W2034763810 modified "2023-09-27" @default.
• W2034763810 title "Acid—base chemistry of α-alkylcobalamins. Determination of additional formation constants for the ‘tuck-in’ species of base-off cobalamins" @default.
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• W2034763810 doi "https://doi.org/10.1016/s0020-1693(00)85526-7" @default.
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