Galactaric acid 2-deoxy

Escherichia coli metabolizes D-glucaric acid and galactaric acid to give respectively 3-deoxy-D-eryt/zro-2-hexulosaric and 3-deoxy-h-threo-2-hexulosaric acids.268... 

The absolute configuration l(124/35) for natural w6o-quercitol was established by chemical correlation with 3-deoxy-D-a j/Jo-hexaric acid ( 3-deoxy-n-galactaric acid ) and with scyHo-quercitol (29). ... 

Dimerization of 2-amino-3,4,6-tri-0-benzyl-2-deoxy-D-glucose with l.l -thionyl-or sulfonyl-di-imidazole gave the fructosazine and bis-tetrahydropyrano-piper-azine derivatives 73 and 74 in a ratio of 1 5, respectively a related compound appeared in Vol. 25, p.l32. The P-carboline derivative 75, isolated as a natural product from a hybrid plant cell culture product, was synthesized in six steps from tryptamine and ( )-4,5,6-tri-0-acetyl-2,3-dideoxy-D-ery/Aro-hex-2-enose. Thiazolo-triazoles such as 76, termed acyclo-C-nucleosides, were obtained on deacetylation of the product from condensation of peracetylated D-gluconic or galactaric acids with 4-araino-3-aryl-l,2,4-triazole-5-thiols in the presence of POCls. The related 1,2,4-triazole 77 and dihydroimidazole 78 were obtained by condensation of D-glucono-1,5-lactone with aminoguanidine and ethylenedia-mine, respectively, followed by acetylation then O-deacetylation. ... 

Sixteen pentahydroxycyclohexanes are predicted on the basis of stereochemical theory. The configuration of d-quercitol was limited to that shown below by nitric acid oxidation to galactaric (mucic) acid (8 ) and by alkaline permanganate oxidation to 3-deoxy-D-galactaric acid (metasaccharinic acid) (83), This same acid was obtained from Z-viburnitol (58), Hence, the arrangement of hydroxyl groups on carbon atoms 2, 5, and 6 of d-quercitol and Z-viburnitol must be the same. Another series of reactions also led to identical compounds from these two deoxyinositols (53), It was found that Acetobacter suboxydans catalyzed the oxidation of Z-viburnitol to a deoxy-... 

This oxidation, as employed by Posternak, was very useful in elucidating the configuration of the inositols (see above). From mj/o-inositol, S. and T. Posternak obtained DL-talaric and DL-glucaric acids. From myo-inosose-2, T. Posternak obtained DL-idaric acid. In these instances, the ring was opened to form dibasic acids. d-Quercitol was oxidized by Posternak (6S) to 3-deoxy-D-galactaric acid. In all these oxidations, it was necessary to maintain low temperatures. 

Deoxy-D-galactaric acid forms a monolactone readily 52), whereas... 

Diulose and Acid derivatives.- D-threo-hexo-2,5-diulose dimer (full report see Vol. 10, p. 108), galactaric acid, L-ascorbic acid 2-O-phosphate, D-erythronic acid 3,4-carbonate, and methyl (methyl 3-deoxy-D-arabino-2-heptulopyranosid) onate. Single crystal X-ray analysis has been used to study the dehydration of crystalline D-glucuronamide hydrate. ... 

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