There have been many attempts to illuminate glycoconjugate interactions using diazirine photocrosslinkers to form covalent abducts to allow for more facile separation and identification. A limitation of this process is the lack of specificity of the abduct formation by the photocrosslinker. In attempt to direct photocrosslinking, the incorporation of deuterium around the diazirine has been attempted. The incorporation of the deuterium is intended to slow the abduct formation, increasing the amount of covalently captured moiety of interest.Several efforts towards the synthesis of vinaxanthone, a promoter of nerve regeneration after spinal cord injury, have been made. Starting from vanillin, steps were taken to fabricate a large amount of a key intermediate, an enaminone. A bromination, ether formation and a Baeyer-Villiger oxidation were performed to afford a formate group. The phenol was then produced and a Fries rearrangement was performed, followed by enaminone formation with DMF-DMA, with reasonable yeild.

Attempts at modifying diazirine glycoconjugate photocrosslinkers for efficacy and progress towards the synthesis of a novel promoter of nerve regeneration

243rd National Meeting (2012)

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