Preparation of Dicyano- and Methylcobinamide from Vitamin B12a

Abstract Treatment of vitamin B 12a 1 (hydroxycobalamin hydrochloride, aquocobalamin) with NaBH 4 and ZnCl 2 leads to the selective cleavage of the nucleotide loop and gives dicyanocobinamide 2A in good yield. Methylcobinamide 4 was prepared from 2 via aquocyanocobinamide 3. The glutathione-mediated...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2008-11, Vol.2008 (21), p.3429-3432
Main Authors: Wedemeyer-Exl, Christina, Darbre, Tamis, Keese, Reinhart
Format: Article
Language:English
Online Access:Get full text
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Summary:Abstract Treatment of vitamin B 12a 1 (hydroxycobalamin hydrochloride, aquocobalamin) with NaBH 4 and ZnCl 2 leads to the selective cleavage of the nucleotide loop and gives dicyanocobinamide 2A in good yield. Methylcobinamide 4 was prepared from 2 via aquocyanocobinamide 3. The glutathione-mediated methylation of 3 in a pH 3.5 buffer solution proceeded with MeI, but not with MeOTs.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0028-1083187