Photorelease of carboxylic acids from vitamin B6-derived photocages
LE3 .A278 2015
Bachelor of Science
Most photoprotecting groups used in photochemical reactions can be toxic or inert after the reaction has taken place and are left in the body. Pyridoxine (Vitamin B6) is an essential vitamin required for human life and has a structure that is very attractive for use as a photoprotecting group. Molecules that have a similar structure to pyridoxine, such as ortho-hydroxybenzylalcohol are effective photoprotecting groups. We attempted to use pyridoxine as a photoprotecting group and test its photochemical properties. (5-hydroxy-6-methylpyridine-3,4-diyl)dimethanediyl diacetate (4) was synthesized at a yield of 91 %. This product was characterized using 1H NMR, and UV/Vis. The product (4) was irradiated with 300 nm light under near biological conditions to study its photochemistry. It was found that pyridoxine is formed in a yield of 23 % over 40 minutes. Pyridoxine meets many of the criteria for an effective photoprotecting group such as aqueous solubility, dissociation and stability of the leaving group, appropriate excitation wavelength, high yield, and inertness in the dark. The experiments done are important for understanding the release mechanism of the acetic acid group and will serve as a model for the more complex carboxylic acid groups that will be used in the future.
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