“Clickable” Vitamin B12 Derivative |
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Authors: | Mikołaj Chromiński Prof. Dorota Gryko |
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Affiliation: | 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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Keywords: | click chemistry cobalamin copper cycloaddition vitamin B12 |
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