CLXXII.—Constitutional studies in the monocarboxylic acids derived from sugars. Part V. Hexonic and pentonic acid amides. The action of sodium hypochlorite on the isomeric trimethyl arabonamides

Humphreys, Robert W. R.; Pryde, John; Waters, E. T.

doi:10.1039/jr9310001298

Cited by 10 publications

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“…Bromine oxidation yielded a sirupy lactone which was converted to a crystalline amide in methanol saturated with ammonia. Recrystallization of t h e amide from butanone yielded a product whose melting point was 154-155 "C, unchanged when the sample was mixed with authentic 2,3,5,6-tetra-0-inlethyl-u-galactonamide (22). …”

Section: Preparative Papermentioning

confidence: 99%

The Water-Soluble Polysaccharides of Dermatophytes: Iv. Galactomannans I From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

Bishop¹,

Perry²,

Blank³

et al. 1965

Can. J. Chem.

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A group of polysaccharides, called galactomannans 1,'-were precipitated as their insoluble copper conlplexes from aqueous solutions of the crude polysaccharides obtained from each of the orgar~isms designated in the title. T h e five galactomannans I were hon~ogeneous under conditions of electrophoresis and ultracentrifugation and had high positive specific rotations. T h e major constituent monosaccharide was D-mannose; amounts of D-galactose ranged from nil for the polysaccharidc from T. rubrz~nz to 13% for that fro111 T. schotsleinii. Methylation and hydrolysis of the five galactomannans I yielded varying amounts of the following: 2,3,5,6-tetra-0-methyl-D-galactose (not present in the products from T. The objective of this continuing program on polysaccharides of dermatophytes is to relate polysaccharide structure to species differences and immunological properties. As reported previously (I), preliminary examination of five dermatophytes showed that each had a similar pattern of water-soluble polysaccharides, specifically, two galactomannans and a glucan. At present the investigations will be limited t o comparisons of gross structural features of the polysaccharides in each of the above three groups as revealed by methylation and periodate oxidation studies. The results of immunochen~ical tests may necessitate niore detailed studies of fine structure a t a later stage.The present paper describes the isolation and gross structural features of one group of Crude polysaccharides were extracted from powdered cells of the organisms in yields of 5-10% a s described previously for T. granulosum (2). T h e products were tan-colored 'Issued as N.R.C. No. 8201.

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Section: Preparative Papermentioning

confidence: 99%

The Water-Soluble Polysaccharides of Dermatophytes: Iv. Galactomannans I From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

Bishop¹,

Perry²,

Blank³

et al. 1965

Can. J. Chem.

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“…Oxidation by bromine water yielded a syrupy lactone, which was converted into an amide in methanol saturated with ammonia. The amide crystallized spontaneously after evaporation of the solvent and was recrystallized from butanone to yield 2,3,5,6-tetra-0-methyl-D-galactonamide (17), m.p. 155-156 "C, [a]n2' +6O (c, 3 in water).…”

Section: Imetkylation Of Galactoma?znans 11mentioning

confidence: 99%

The Water-Soluble Polysaccharides of Dermatophytes: V. Galactomannans Ii From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

Bishop¹,

Perry²,

Blank³

et al. 1966

Can. J. Chem.

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I t was reported earlier that each of five derlllatophytes had a similar pattern of watersoluble polysaccharides, specifically, two galactoinanilans and a glucan (I). The previous paper in this series described the properties and gross structural features of one group of the galactornannans (called galactomannan I) (2).The present paper describes the separation of the three groups of polysaccllarides and reports the properties and gross structural features of the second group of galactomailnans (called galactomannan 11) from Trichopkyton granuloszlm Sabouraud, 1909, Trichophyton interdigitale Priestley, 1917 Guiart and Grigorakis, 1928, I'rickophyton r z~b r u m (Castellani) Sabouraud, 1911, and Trichoplzyton schonleinii (Lebert) Langeron and h~Iilochevitch, 1930. Crude polysaccharides were extracted from powdered cells of the organisills in yields of 5-10% as described previously for T . granulosz~m (3). The procedure \vas designed to yield pol>-saccharide preparations which were free of lipid and protein.T h e airn of this continuing program is to relate structures to serological properties in the polysaccharides from dermatophytes. The presence of any contatniilating lipid or protein, bound or free, could interfere in the serological tests and cause difficulties in interpreting the results of structural studies. The crude polysaccharides \\-ere resolved into t~o galacton~ailnails and a glucan by the procedure shown in Reaction Scheme 1. Addition of Fehling solution to aqueous solutions of the crude polysaccharides precipitated galactomannans I as insoluble copper coinplexes (2). The polysaccharides ~vhich were soluble in Fehling solution were recovered and lIssiled as N.R.C. No. 9108.

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“…[M]21' +70 in acetone (c, 0.96) [Humphreys et al 1931]. (Found: C, 47-7; H, 8-5; N, 5'4; OMe, 48.8 %.…”

mentioning

confidence: 99%

Polysaccharides synthesised by micro-organisms

Haworth

Raistrick

Stacey

1937

Biochemical Journal

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CLXXII.—Constitutional studies in the monocarboxylic acids derived from sugars. Part V. Hexonic and pentonic acid amides. The action of sodium hypochlorite on the isomeric trimethyl arabonamides

Cited by 10 publications

References 0 publications

The Water-Soluble Polysaccharides of Dermatophytes: Iv. Galactomannans I From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

The Water-Soluble Polysaccharides of Dermatophytes: Iv. Galactomannans I From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

The Water-Soluble Polysaccharides of Dermatophytes: V. Galactomannans Ii From Trichophyton Granulosum, Trichophyton Interdigitale, Microsporum Quinckeanum, Trichophyton Rubrum, and Trichophyton Schönleinii

Polysaccharides synthesised by micro-organisms

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