Sodium periodate, reaction with carbohydrates

Bacterial and Fungal Glycoproteins. — No evidence has been found to substantiate the claim for the presence of covalently-bound carbohydrate in energy-transducing adenosine triphosphatases of Escherichia coli. Incomplete removal of sodium dodecyl sulphate (SDS) after SDS-electrophoresis of the protein results in a positive reaction with the periodate-Schiff staining method. 

The carbohydrate derived nitroalkene 351 undergoes Diels-Alder reaction with 1,3-butadiene to afford 352, while 354 leads to a reversal of the diastereoselec-tivity giving 355 as the major products. However, the diastereoselectivity was modest with ratios of 78 22 and 67 33 for these two reactions. Denitration, acidic deacylation, sodium periodate cleavage and final reduction provided the (5) and R) alcohols 353 and 356 respectively (Scheme 55). ... 

Regioselective Oxidation. Following the original discovery by David and Thieffrey, several stannylenes have been oxidized by bromine to acyloins (eq 8). Hanessian employed this reaction for the synthesis of a densely functionalized intermediate which was converted into (-i-)-spectinomycin. A detailed study of monooxidation of unprotected carbohydrates has also appeared. Stannylenes are oxidized the same way as diols, with Sodium Periodate and Lead(IV) Acetate. ... 

The benzyl group has been widely used for the protection of hydroxyl functions in carbohydrate and nucleotide chemistry (C.M. McCloskey, 1957 C.B. Reese, 1965 B.E. Griffin, 1966). A common benzylation procedure involves heating with neat benzyl chloride and strong bases. A milder procedure is the reaction in DMF solution at room temperatiue with the aid of silver oxide (E. Reinefeld, 1971). Benzyl ethers are not affected by hydroxides and are stable towards oxidants (e.g. periodate, lead tetraacetate), LiAIH, amd weak acids. They are, however, readily cleaved in neutral solution at room temperature by palladium-catalyzed bydrogenolysis (S. Tejima, 1963) or by sodium in liquid ammonia or alcohols (E.J. Rcist, 1964). 

A method for the determination of formaldehyde in the presence of acetaldehyde was developed by Nicolet and Shinn.88,100 103 After the excess periodate had been destroyed, these workers swept the acetaldehyde (from the neutral reaction mixture) into a sodium bisulfite solution by means of a stream of carbon dioxide. The acetaldehyde was measured by conventional, bisulfite methods, and the residual formaldehyde was precipitated with Dimedon. This procedure was applied to protein hydroly-zates and to terminal deoxy structures of carbohydrates.88,280 ... 

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