Synthetic Approaches toward Vitamin B₁₂ Conjugates.

Wierzba, Aleksandra J.; Hassan, Sidra; Gryko, Dorota

The ability to conjugate functional molecules to vitamin B12 (cobalamin) is an important strategy for the construction of hybrid molecules with various applications in medicinal chemistry, diagnostics, and biological sciences. Cobalamin, as an exogenous compound, reaches mammalian cells via a system of transport proteins and therefore the position of conjugation must be selected in such a way that the recognition process is not disturbed. The complex structure of vitamin B12 provides many routes for the synthesis of conjugates containing cargos appended at different sites, however, only the e‐propionamide chain, β‐axial position and R5′‐OH are found to meet the aforementioned criteria. Over the years, a number of synthetic approaches leading to cobalamin conjugates have been developed and, herein, we summarize those leading to conjugates with a cargo tethered at the central cobalt ion, macrocyclic core, ribonucleotide moiety, or a combination thereof. Vitamin B12 is an essential nutrient to all mammals and certain bacteria. Consequently, it is an attractive natural vector. To this end, a number of synthetic approaches leading to cobalamin conjugates have been developed and herein, we summarize those leading to conjugates with a cargo tethered at the central cobalt ion, macrocyclic core, ribonucleotide moiety, or a combination thereof.

VITAMIN B12; PHARMACEUTICAL chemistry; MACROCYCLIC compounds

Asian Journal of Organic Chemistry, 2019, Vol 8, Issue 1, p6

2193-5807

Academic Journal

10.1002/ajoc.201800579