Benzimidazole, carbohydrate derivatives

The term C-nucleoside was only coined after isolation and characterization of the first member of this class pseudouridine, in 1975 [97ACH(ip)]. Before that, alditolyl derivatives of some heterocycles (acyclo C-nucleo-sides) were known both as natural products (alditolyl pteridines or biopterins) as well as products of syntheses (e.g., alditolyl derivatives of imidazoles, benzimidazoles, thiazoles, benzothiazoles, 1,2,3-triazoles, quinoxalines, and flavazoles) and were classified as carbohydrate derivatives of heterocyclic compounds. After isolation of pseudouridine, other naturally occurring members were successively isolated, characterized, and synthesized. It is worth mentioning that synthesis preceded isolation in two cases 9-dea-zaadenosine and pyrrolosine. Comparison with the synthetic compounds facilitated structure elucidation in one case (9-deazaadenosine) and structure reassignment in the other (pyrrolosine). 

The fourth student in this group, Stanford Moore, began his doctoral thesis research with Link in 1935. His work involved the development of a new, and still useful, procedure for oxidizing aldoses to the aldonic acids by potassium hypoiodite in methanol solution the resulting aldonic acids were then converted into nicely crystalline benzimidazole derivatives that proved more suitable for the characterization of carbohydrates than the classical osazones. This method, developed by Moore and Link (1940), was extended to the characterization of hexuronic acids, as their bis(benzimidazole)s, after oxidation to the glycaric acid (R. Lohmar, Dimler, Moore, and Link, 1942), of lactic acid (Moore, Dimler, and Link, 1941 Dimler and Link, 1942), and of ribose, fucose, and digitoxose (Dimler and Link, 1943). During these... 

Benzimidazole Derivatives.—In recent years benzimidazole glycosides have become of interest in the chemistry of anti-pernicious anemia factors. This interest prompted Petrow and his colleagues226 to prepare benzimidazole glycosides with 2-desoxysugars as the carbohydrate component. 

For a review of the substituted benzimidazoles derived from the sugar acids see N. K. Richtmyer, Advances in Carbohydrate Chemistry, 6, 175 (1951). 

M3. Moore, S., and Link, K. P., Carbohydrate characterization. I. The oxidation of aldoses by hypoiodite in methanol. II. The identification of. seven aldo-mono-saccharides as benzimidazole derivatives. /. Biol. Cham. 133, 293-311 (1940). 

Kazimierczuk Z, Dudycz L, Stolarski R, Shugar D (1981) Synthesis and conformation of halogeno benzimidazole nucleosides-fluoro-derivative and iodo-derivative. J Carbohydr Nucleosides Nucleotides 8(2) 101-117... 

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