D-Galactose oxidation

From Vandenheede et al. (1972), reproduced with permission. b The D-galactose-oxidized treated preparation had 91% of the activity of the native glycoprotein. 

The structure of compound A was established in part by converting it to known compounds Treat ment of A with excess methyl iodide in the presence of silver oxide followed by hydrolysis with dilute hydrochlonc acid gave a tnmethyl ether of D galactose Companng this trimethyl ether with known trimethyl ethers of D galactose allowed the structure of compound A to be deduced... 

Oxidation of tiie caibon atoms at both ends of the carbon chain produces an aldaric acid. That made from D-galactose is galactaric acid [526-99-8] a... 

Deoxy-sugars. Part XXII. Comparative Rates of Oxidation and Reduction of D-Galactose and 2-Deoxy-D-galactose," W. G. Overend, F. Shafizadeh, and M. Stacey, J. Chem. Soc., (1951) 2062-2064. 

AW, Acid-washed Choi, Cholesterol DMAP, 4-(Dimethylamino)pyridine DMF, N,/V-Dimethylformamide DMTr, Di(p-niethoxyphenyl)phenyl methyl GalNAc, N-Acetylgalactosamine, 2-acetamido-2-deoxy-D-galactose HMF, 5-Hydroxymethylfur-fural, 5-(hydroxymethyl)-2-furaldehyde INOC, Intramolecular nitrile oxide-alkene cycloaddition Lea, Lewisa Lex, Lewisx MOM, Methoxymethyl MP, p-Methoxyphe-nyl MS, Molecular sieves NIS, N-Iodosuccinimide PCC, Pyridinium chlorochromate PDC, Pyridinium dichromate PMA, Phosphomolybdic acid PMB, p-Methoxybenzyl ... 

Selective Oxidation of Terminal B-D-Galactose (or N-acetyl-galactosamine) Groups... 

The sirup and the crystalline acid (VIII), when oxidized with sodium periodate, gave the same aldehydes as those produced by the oxidation of the ester from D-glucose (II) and its saponification product (XXX), respectively. Hence, the mechanism of the reaction of D-galactose is the same as that of D-glucose and D-mannose. Moreover, the approximate yield from... 

Neither has oxidation, with lead tetraacetate, of the sirup obtained by dehydration of the D-galactose condensate VIII so far resulted in isolation of the expected dialdehyde. On the other hand, when the anhydride from the D-glucose condensate (XXXIV) was oxidized with lead tetraacetate, an appreciable amount of dialdehyde (XXXVI) was isolated. This discrepancy in behavior is probably attributable to the trans position of the hydroxyl groups of the anhydride derived from D-galactose as compared with the cis configuration for the anhydride from D-glucose. 

By analogy with the biosynthesis of L-ascorbic acid and with other oxidation-reduction enzyme systems, it seems likely that D-galactose is oxidized to D-galacturonic acid (XXIII) on reduction at Cl, this yields L-galactonic acid (XXIV), the 1,5-lactone (XXV) of which, on reduction at Cl, would give L-galactose (XXII). 

The immunological properties of a modified S14, obtained on treatment with D-galactose oxidase and subsequent oxidation of the aldehyde group to a carboxyl group with chlorite, have been investigated.45... 

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