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Vitamin B12 Derivatives For Orthogonal Functionalization.

M. Chromiński, Agnieszka Lewalska, Maksymilian Karczewski, D. Gryko
Published 2014 · Chemistry, Medicine

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The synthesis of vitamin B12 derivatives for selective orthogonal conjugation at both the Co center and 5'-OH is reported. Newly developed, reduction-free, direct alkynylation of vitamin B12 at the central cobalt ion proved to be versatile, with the formed acetylides, unlike other metalloorganic derivatives, showing remarkable heat and light stability, thus making them promising candidates as a drug carrier. Subsequently, high-yielding functionalization can be achieved via a sequence of selective [1,3] dipolar azide-alkyne cycloadditions (AACs) or carbamate formation followed by AAC.
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