Amino hexuronic acids

Acetamido-2-deoxy-D-galacturonic acid, a major immunogenic component of Salmonella typhosa [2], was the first naturally occurring amino hexuronic acid identified [3]. In 1962 Perkins reported that the cell wall of Micrococcus lysodeikticus... 

III. SYNTHETIC STUDIES OF PYRANOSYL SUGAR AMINO ACIDS A. Syntheses of Natural Amino Hexuronic Acids... 

Hetero-Diels-Alder reactions have been used in the construction of amino-sugars, asymmetry being induced by the use of either a chiral Lewis acid catalyst or a chiral auxiliary. Thus, the 3-amino-hexuronic acid derivatives 61 were obtained with high de and ee using a copper(II) triflate catalyst with a chiral bisoxazoline ligand. 4-Amino-4-deoxy-D-erythrose and 4-amino-4,5-dideoxy-L-lyxose (63), the latter a potent inhibitor of a-L-fucosidase, were obtained from the D-pyroglutamic add-containing diene 62 (Scheme 19). ... 

Epimerization at C-5 of hexuronic acids is a reaction that proceeds both on the polymer and on the sugar nucleotide level. In addition to the three pairs of parent acids, namely, the u-glucolL-ido-, D manno/L-gulo-, and D-ga-lacto/L-altro-he uron c acids, the 2-amino-2-deoxy acids belonging to the last two and the 2,3-diamino-2,3-dideoxy acids belonging to the middle pair have been found. 

It will be appropriate to consider first the building units of the carbohydrate residues and it will be immediately apparent that D-mannose and D-galactose with N-acetyl-amino sugars and hexuronic acids play a predominant role. It is proposed, therefore, to discuss briefly some of the more important discoveries connected with the two latter groups and with the carbohydrate sulfates. 

It seems probable that other L-hexuronic acids listed in Table III, such as L-iduronic,208 2-amino-2-deoxy-L-altruronic,209 and 2,3-diamino-2,3-dideoxy-L-guluronic210 acids may arise in bacterial polymers as a result of epimerization at C-5 at the polymer level. Such a pathway was demonstrated for the biosynthesis of L-idosyluronic acid residues in glycosaminoglycans of higher animals.211 212... 

Saccharides Containing Residues of Amino Sugars and of Hexuronic Acids... 

Hollingsworth, R.I., Lill-Elghanian, D.A. Isolation and characterization of the unusual lipopolysaccharide component, 2-amino-2-deoxy-2-JV-(27-hydroxyoctacosanoyl)-3-0-(3-hydroxy-tetradecanoyl)-gluco-hexuronic acid, and its de-O-acylation product from the free lipid A of Rhizobium trifolii ANU843. J Biol Chem 264 (1989) 14039-14042. 

Hexulosonic acid, Z-deoxy-o-erythro-, 6-phosphate, 253, 255 Z-deoxy-D-threo-, 263 Hexuronic acid, aminodeoxy-, 293 —, poly amino-, 273... 

Meyer and Wolfrom and their coworkers detected the uronic acid in the barium acid salt of heparin both qualitatively and quantitatively, and considered it to be the source of the acidity in the acid salt. Amino sugar was also estimated. These results, which cannot be said to be as precise as the elemental data, indicate a ratio of 1 1 for amino sugar and hexuronic acid. 

Amino-3,4-dideoxy-D-j y/o-hexuronic acid (ezaminuroic acid) is a component of antibiotic ezomydn A2. The methyl glycoside of another antibiotic sugar belonging to the 4-deoxyhexose family, 4-deoxy-DL-neosamine C (in form of its peracetylated derivative 350) was synthesized from the butyl ester 279 (R = Me,R = COzBu) according to the route shown. 

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