Lyxuronic acid

All of the micro-organisms that had been reported before 1964 proved to be less than satisfactory for the production of 96 from D-glu-cose. Among the drawbacks associated with some of the micro-organisms were (a) the production of colored bodies, (b) the generation of such byproducts504-508 as comenic acid (98), rubinic acid (99), rubin-inol (100),504,507 508 and D-lyxuronic acid (101),509 and (c) the use of special procedures to prepare the cells in order to obtain 96. 

R. K. Hulyalkar and M. B. Perry, t-Lyxuronic acid, L-lyxose, and 5-deoxy-L-lyxose, Cart J. Chem., 43 (1965) 3241-3246. 

Periodate oxidation of l-0-benzoyl-2,3-0-isopropylidene-a-D-mannofuranose has afforded access to several derivatives of D-lyxuronic acid, and glyco-furanosyl halides of D-riburonic acid, which are of value in nucleoside synthesis, have been made by way of the corresponding thiofuranosides (see Chapter 7). 

Methyl lyxoside Lyxitol Lyxonic acid Lactone Lyxuronic acid Methyl ester Deoxy... 

Uronic acids of the pentose series have been prepared by the oxidative degradation of amides. Mucic acid monoamide can be converted by the action of hydrogen peroxide and iron salts or by hypobromite to the corresponding lyxuronic acid 63), The acids were isolated as the phenylosa-zone-phenylhydrazides, or as the tetraacetates of the amide. 

Ameyama M, Kondo K (1958a) Carbohydrate metabolism by Acetobacter species. Part III. Isolation and identification of D-lyxuronic acid on glucose oxidation by A. melanogenum. Bull Agric Chem Soc Jpn 22(6) 380-386... 

Various nucleoside 5 -carboxylic acids have been prepared from glycosyl chlorides of methyl D-riburonate and methyl D-lyxuronate. Other groups have reported the synthesis of uridine a-nucleoside analogues from 2-alkoxy-carbonyl-5-chloro-tetrahydrofuran and 5-substituted uracils, e.g., (56), and D-glucuronyl derivatives of 5-fluoro-uracil. ... 

Methyl L-lyxuronate, L-78 Methyl a-i>niannopyranosiduronaniide, M-I23 Methyl a-i>niannopyranosiduronic acid, M-I23 Methyl a-i>niannopyranosidurono-6,3-lactone, M-123 Methyl 4-0-mesyl-2,3-di-0-niethyl-p-D-glucopyranosiduronic acid, M-192 Methyl 2-0-mesyl-p-i>glucofuranosiduronamide, G-537 Methyl (methyl 4-0-acetyl-2,3-di-0-methyl-P-D-glucopyranosid)uronate, M-192... 

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