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“Clickable” Vitamin B12 Derivative

Authors

  • Mikołaj Chromiński,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 22-632-6681
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  • Prof. Dorota Gryko

    Corresponding author
    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 22-632-6681
    • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw (Poland), Fax: (+48) 22-632-6681
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Abstract

A “clickable” vitamin B12 derivative possessing the azide functionality at the 5′-position was synthesized by means of a two-step procedure on the gram scale. The reaction of cobalamin with mesyl chloride (MsCl) afforded the 5′-OMs derivative, which was subsequently transformed to the desired 5′-azide, the structure of which was confirmed using X-ray analysis. It proved to be reactive in the azide–alkyne 1,3-dipolar cycloaddition reaction to give substituted triazoles in high yields. A study of the reaction conditions and the scope of the process are reported.

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