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“Clickable” Vitamin B 12 Derivative
Author(s) -
Chromiński Mikołaj,
Gryko Dorota
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203899
Subject(s) - azide , derivative (finance) , chemistry , cycloaddition , combinatorial chemistry , alkyne , cobalamin , click chemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , vitamin b12 , financial economics , economics
A “clickable” vitamin B 12 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.