XXVII.—Crystalline form of the calcium salt of the new optically active glyceric acid

The cyclization (internal Henry addition) of 6-deoxy-3-O-methyl-6-nitro-D-glucose (1) and-L-idose (2) was investigated with respect to the sequence in which stereoisomeric deoxynitroinositol methyl ethers are formed from each. It was found that, under conditions of kinetic control, the primary products generated from 1 are the nitronate 4′ (that corresponds to the epimeric deoxynitroinositols 4 and 5 having the epi-3 and muco-3 configurations, respectively) and the nitronate D-6′ of optically active 1-deoxy-4-O-methyl-1-nitro-L-myo-inositol (L-6). They are formed in approximately equal proportions. Ensuing thermodynamically controlled processes lead to racemization of L-6 and formation of the scyllo isomer 3 at a relatively slow rate. The cyclization of 2, found to be faster than that of 1, gave as primary products the enantiomeric nitronate D-6′ and the nitronate 3′ in a ratio of about 4:1. The nitronate 4′ arose by subsequent epimerization. The optically active compounds D-6 and L-6 were isolated in pure, crystalline form.

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Microbial resolution of DL-N-benzyloxycarbonyl-p-hydroxyphenylglycine by Streptomyces zaomyceticus

Canadian Journal of Microbiology ◽

10.1139/m84-208 ◽

1984 ◽

Vol 30 (10) ◽

pp. 1301-1304 ◽

Cited By ~ 1

Author(s):

Yasuji Suhara ◽

Sayuri Itoh ◽

Kazuteru Yokose ◽

Rieko Ninomiya ◽

Kimihiro Watanabe ◽

...

Keyword(s):

Optically Active ◽

Crystalline Form ◽

Soil Organism ◽

Unique Type

Using DL-p-hydroxyphenylglycine umbelliferone carbamate as the probe, screening from soil was carried out for microbes capable of hydrolysing urethane-type derivatives. Out of 71 strains positive for umbelliferone liberation (fluorescent), 8 strains were able to hydrolyze DL-N-benzyloxycarbonyl-4-hydroxyphenylglycinc (I). One of such soil organism identified as Streptomyces zaomyceticus carried out this reaction in an enantio-selective manner. Optically active, pure D-N-benzyloxycarbonyl-4-hydroxyphenylglycine and L-4-hydroxyphenylglycine were obtained in crystalline form in 83 and 80% yields, respectively, after a 5-day incubation of the substrate (300 mg/100 mL) with this organism. In contrast to conventional L-acylase (EC 3.5.1.14) which can hydrolyze N-pbenylacetyl-4-hydroxyphenylglycine but not I, the enzymes responsible for the above resolution could cleave both substrates, indicating that they represent a unique type of amidohydrolase.

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The bacterial production of acetylmethylcarbinol and 2.3-butylene glycol from various substances.―II

Proceedings of the Royal Society of London. Series B, Containing Papers of a Biological Character ◽

10.1098/rspb.1912.0028 ◽

1912 ◽

Vol 85 (576) ◽

pp. 73-78 ◽

Cited By ~ 4

Keyword(s):

Nitric Acid ◽

Bacterial Production ◽

Culture Media ◽

Crystalline Form ◽

Volatile Substance ◽

Glyceric Acid ◽

Bacterial Fermentation

The action of B. Subtilis (Cohn), B. mesentericus vulgatus (Flügge) ( B. vulgatus (Flügge) Migula), and Tyrothrix tenuis (Duclaux) ( B. tenuis (Duclaux) L. and N.) on various substances has been investigated by Péré (1). This observer, on distilling his various culture media, obtained lævo-rotatory distillates strongly reducing to Fehling’s solution. In all cases he concluded that the volatile substance present was glyceraldehyde, and upon his results based a theory that sugars undergoing bacterial fermentation break down primarily to a triose, that is to say, glycerose. He was, however, unable to characterise his compound satisfactorily; for example, it did not give Schiff’s reaction, no osazone was obtainable, and although in some cases he obtained small quantities of lead, calcium, and barium salts of an acid formed by the oxidation of his volatile substance with nitric acid, which he took for salts of glyceric acid, the quantities analysed were so small that no reliance can be placed upon the results. Moreover, none of his salts was obtained in crystalline form.

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Urinary sediments in sheep feeding on oestrogenic clover. III.* The identification of 4′-O-methyl equol as a major component of some sediments

Australian Journal of Agricultural Research ◽

10.1071/ar9740509 ◽

1974 ◽

Vol 25 (3) ◽

pp. 509 ◽

Cited By ~ 8

Author(s):

MC Nottle ◽

AB Beck

Keyword(s):

Calcium Salt ◽

Optically Active ◽

The Other ◽

Biochanin A ◽

Chemical Identification ◽

Main Metabolite ◽

First Report

Chemical identification has been made of two types of sediment formed in the urine of sheep ingesting clovers high in formononetin. One type, described previously, consists of the calcium salt of the glucuronide of 4′-O-methyl equol (4′-methoxy-7-isoflavanol). The other contains unconjugated 4′-O-methyl equol associated with small amounts of equol, formononetin and biochanin A. This is the first report of the isolation of optically active 4′-O-methyl equol. The present findings indicate that, under some conditions, at present undefined, 4′-O-methyl equol may replace equol as the main metabolite of formononetin. When administered subcutaneously into mice, 4′-O-methyl equol is slightly less oestrogenic than equol, and its possible role in 'clover disease' of sheep is discussed. ____________________ *Part II, Aust. J. Agric. Res., 23: 693 (1972).

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ChemInform Abstract: Synthesis of Optically Active Glyceric Acid Derivatives from Ascorbic Acids.

ChemInform ◽

10.1002/chin.199534111 ◽

2010 ◽

Vol 26 (34) ◽

pp. no-no

Author(s):

P. H. J. CARLSEN ◽

K. MISUND ◽

J. ROEE

Keyword(s):

Optically Active ◽

Glyceric Acid ◽

Ascorbic Acids

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Synthesis of Optically Active Glyceric Acid Derivatives from Ascorbic Acids.

Acta Chemica Scandinavica ◽

10.3891/acta.chem.scand.49-0297 ◽

1995 ◽

Vol 49 ◽

pp. 297-300 ◽

Cited By ~ 7

Author(s):

Per H. J. Carlsen ◽

Kristin Misund ◽

Johan Røe ◽

Enrique Colacio ◽

Harri Lönnberg ◽

...

Keyword(s):

Optically Active ◽

Glyceric Acid ◽

Ascorbic Acids

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A Convenient, Scalable Process for the Preparation and Purification of Calcium Acamprosate

Synthesis ◽

10.1055/s-0040-1707399 ◽

2020 ◽

Vol 52 (19) ◽

pp. 2828-2832

Author(s):

Guido Furlotti ◽

Claudia Cavarischia ◽

Alex Comely ◽

Marta Écija ◽

Tommaso Iacoangeli ◽

...

Keyword(s):

Alcohol Dependence ◽

Cation Exchange ◽

Potassium Chloride ◽

Calcium Salt ◽

Crystalline Form ◽

One Pot ◽

Selective Precipitation ◽

Step Process ◽

Dimethylformamide Solution

Calcium acamprosate (Campral, N-acetylhomotaurine calcium salt) is a well-established drug for the treatment of alcohol dependence. Its preparation is generally based on a three-step process with some remarkable drawbacks. To avoid these flaws, we have developed a direct, scalable, one-pot procedure for the preparation of calcium acamprosate entailing the nucleophilic opening of readily available 1,3-propanesultone with potassium acetamide (from acetamide and potassium tert-butoxide) in N,N-dimethylformamide solution, followed by in situ cation exchange by addition of calcium chloride at controlled pH, addition of 2-propanol (IPA) as a cosolvent, and removal of potassium chloride by selective precipitation. Calcium acamprosate (purity higher than 95%) is thus obtained in the commercial crystalline form in 74–77% yield.

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