title: "Clickable" vitamin B12 derivative.
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.
authors: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors: Mikołaj
authors: M
authors: Chromiński
authors: Dorota
authors: D
authors: Gryko
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014805:Vitamin B 12 / Q000138:chemical synthesis* / Q000737:chemistry; D014803:Vitamin B Complex
chemical_list: D000480:Alkynes; D001386:Azides; D014230:Triazoles; D014803:Vitamin B Complex; D014805:Vitamin B 12