Vitamin B12: chemical modifications

Abstract

Vitamin B12 plays a key role in many metabolic processes occurring in all mammals. Over the years its biological role has been extensively studied generating a lot of interest in the chemistry of this vital molecule. This established a variety of new methodologies for the synthesis and analysis of new cobalamin derivatives as well as creative purification techniques. This tutorial review summarizes all the advancements made in this area, providing a deeper insight into vitamin B12 chemistry.

Recent trends in the development of vitamin B12derivatives for medicinal applications

“…Its lifesaving effect was first noticed during treatments of deadly pernicious anaemia with (B 12 -containing) raw liver extracts in the beginning of the 20 th century. [1][2][3][4][5][6] Taking Before discussing the topics in more detail, a short overview on the structure, properties and biological behaviour of cobalamins (Cbls) is given in chapters 1.1 and 1.2. Today, the chemistry, biochemistry and enzymology of cobalamins (Cbls) are well explored.…”

Organometallic cobalamin anticancer derivatives for targeted prodrug delivery via transcobalamin-mediated uptake

“…In addition, the poor photo-and thermal stability specific to organometallic cobalamins possessing an alkyl, vinyl or aryl group bound to the Co atom imposed another constraint. 7,10 Nevertheless, metal species such as Pt, Re and Tc complexes could be attached at this position by relying on the ability of Cbl to form heterodinuclear complexes of the general motif {Co-CN-M}. [11][12][13] Although remarkable, these derivatives did not release complexes of identical chemical compositions after reduction of the Co center.…”

The intricacies of the stacking interaction in a pyrrole–pyrrole system

“…Hence, as a heteroatomic planar and electronrich ring, it is a useful recognition element in many biological contexts in which it may be engaged in creation of different sorts of NCI such as hydrogen bonds and pstacking [32,33]. Pyrrole-containing molecules include commonly naturally produced compounds such as chlorophyll, chlorins, vitamin B12 and porphyrinogens [34][35][36]. A pyrrole ring is also a part of tryptamines including serotonin, melatonin and many other biologically important substances [37][38][39][40].…”