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Vitamin B12 Derivatives for Orthogonal Functionalization

Author:
Chromiński, Mikołaj, Lewalska, Agnieszka, Karczewski, Maksymilian, Gryko, Dorota
Source:
Journal of organic chemistry 2014 v.79 no.16 pp. 7532-7542
ISSN:
1520-6904
Subject:
chemical structure, cobalt, cycloaddition reactions, drug carriers, organic chemistry, organic compounds, photostability, vitamin B12
Abstract:
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.
Agid:
5502585