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1H NMR Studies of the isomers of dicyanocobalamin and dicyanocobinamide
Journal article   Peer reviewed

1H NMR Studies of the isomers of dicyanocobalamin and dicyanocobinamide

Prasanna K. Mishra, Raj K. Gupta, Prabhat C. Goswami, P.N. Venkatasubramanian and Amar Nath
Polyhedron, v 1(4), pp 321-325
1982

Abstract

An isomeric form of cyanocobalamin (cyanocobalamin′) discovered earlier has been reported to exhibit conformational differences from the regular form, in the corrin ring, aminopropanol side chain, and the nucleotide base. In the present work, we have attempted to answer the question whether a variation in the puckering of the corrin ring in the new form brings about a conformational change in the nucleotide base or vice versa. Measurements of NMR chemical shifts and spin-lattice relaxation times for a large number of protons show that the two isomeric forms of dicyanocobalamin (where the benzimidazole base is detached from the cobalt atom) exhibit differences in conformation for all the three segments of the molecule, namely, the corrin ring, the amino-propanol chain, and the nucleotide base. NMR studies also indicate the existence of a conformationally different isomer of dicyanocobinamide (where the nucleotide base is completely cleaved off), namely dicyanocobinamide′. The existence of cobinamide′ is confirmed by means of thin layer chromatography. Based on these observations, it is suggested that a significant variation in the puckering of the corrin ring occurs in the new form and brings about a consequent change in the conformation of the nucleotide base through the amino-propanol linkage.

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Collaboration types
Domestic collaboration
Web of Science research areas
Chemistry, Inorganic & Nuclear
Crystallography
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