Carbon-13 nuclear magnetic resonance studies of compounds of the vitamin B₆ group and related pyridine derivatives

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DOIResolve DOI: http://doi.org/10.1139/v75-340
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
1480-3291
Volume53
Issue16
Pages24062412
AbstractThe ¹³C chemical shifts and ¹³C–³¹P spin–spin couplings (where applicable) are reported for pyridoxine, pyridoxamine, pyridoxal, pyridoxamine phosphate, and pyridoxal phosphate. Resonance assignments are made by consideration of substituent chemical shift effects, as tested on an analogous series of pyridine derivatives. Increased shielding of the C4′ and C5′ methylene groups of the vitamin B₆ compounds and the methyl groups of 3,4-dimethylpyridine relative to the predicted values are attributed to steric compression. In aqueous solution pyridoxal exists as the hemiacetal form, although at high pH it is in rapid equilibrium with a significant amount of the aldehyde form. Pyridoxal phosphate exists as the aldehyde at high pH, as the hydrated aldehyde at low pH, and in a slow equilibrium between detectable amounts of both species at pH 4. The ¹³C–³¹P couplings through two bonds lie in the range 4.5 ± 0.5 Hz found for a variety of other organic phosphates. The couplings through three bonds indicate a preference for a trans arrangement of the phosphorus and ring carbon-5.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada
Peer reviewedYes
NRC number14679
NPARC number23001406
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Record identifier793f69b9-460d-4cfc-a098-7957e408c998
Record created2017-02-02
Record modified2017-02-02
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