scholarly journals 2-O-methyl-D-glucuronic acid, a new hexuronic acid of biological origin

1976 ◽  
Vol 155 (1) ◽  
pp. 181-185 ◽  
Author(s):  
J H Kieras ◽  
F J Kieras ◽  
D V Bowen
Keyword(s):  
Chemical Ionization ◽  
Glucuronic Acid ◽  
Extracellular Polysaccharide ◽  
Red Alga ◽  
British Library ◽  
Ionization Mass ◽  
Biological Origin ◽  
Hexuronic Acid ◽  
Authentic Compound ◽  
Hydrolysis Of

Acid hydrolysis of the extracellular polysaccharide of Porphyridium cruentum (a unicellular red alga) produced a mixture of aldobiuronic acids and free hexuronic acids. Fractionation of this mixture on an ion-exchange column yielded a hexuronic acid characterized as the title compound. Its identity was confirmed by chromatographic comparisons with the authentic compound, by reduction to the corresponding methylated aldose, by resistance to controlled lead tetra-acetate oxidation and by chemical-ionization mass spectrometry. Complete spectra have been deposited as Supplementary Publication SUP50062 (7 pages) with the British Library (Lending Division), Boston Spa, Wetherby, W. Yorkshire LS23 7BQ, U.K., from whom copies may be obtained under the terms given in Biochem. J. (1976) 153, 5.

STRUCTURE OF THE EXTRACELLULAR POLYSACCHARIDE PRODUCED BY XANTHOMONAS ORYZAE

1962 ◽  
Vol 40 (12) ◽  
pp. 2204-2213 ◽  
Author(s):  
A. Misaki ◽  
S. Kirkwood ◽  
J. V. Scaletti ◽  
F. Smith
Keyword(s):  
Acid Hydrolysis ◽  
Glucuronic Acid ◽  
Periodate Oxidation ◽  
Extracellular Polysaccharide ◽  
Xanthomonas Oryzae ◽  
Sodium Borohydride Reduction ◽  
Glycoside Hydrolysis ◽  
Hydrolysis Of ◽  
Structural Significance ◽  
Molecular Proportion

The extracellular polysaccharide isolated from cultures of Xanthomonas oryzae is composed of D-glucose (5 molecular proportions), D-glucuronic acid (2 molecular proportions), and D-mannose (5 molecular proportions). Acid hydrolysis of this polysaccharide, which contains 0.3% combined pyruvic acid, yields 2-O-β-D-glucopyranosyluronic acid D-mannose, which has been characterized as its crystalline fully methylated β-glycoside. Hydrolysis of the methylated polysaccharide gives 2,3,4,6-tetra-O-methyl-D-mannose (3 molecular proportions), 2,3,4-tri-O-methyl-D-glucuronic acid (1 molecular proportion), 2,3,6-tri-O-methyl-D-glucose (4 molecular proportions), 3,4,6-tri-O-methyl-D-mannose (2 molecular proportions), 2,6-di-O-methyl-D-glucose (3 molecular proportions), 2,3-di-O-methyl-D-glucose (1 molecular proportion). The polyalcohol derived from the polysaccharide by periodate oxidation followed by sodium borohydride reduction gives upon acid hydrolysis glycerol (2 molecular proportions), erythritol (1 molecular proportion), and D-glucose (1 molecular proportion). The general structural significance of these findings is discussed.

THE STRUCTURE OF THE EXTRACELLULAR POLYSACCHARIDE OF AZOTOBACTER INDICUM

1963 ◽  
Vol 41 (11) ◽  
pp. 2826-2835 ◽  
Author(s):  
V. M. Parikh ◽  
J. K. N. Jones
Keyword(s):  
Glucuronic Acid ◽  
Extracellular Polysaccharide ◽  
Molar Ratio ◽  
Linear Molecule ◽  
Partial Hydrolysis ◽  
Major Fraction ◽  
Sodium Metaperiodate ◽  
Unit Reduction ◽  
Hydrolysis Of

The extracellular polysaccharide of the Azotobacter indicum has been shown to be a mixture of two polymers of which the acidic polymer was a major fraction. The acidic polymer contained D-glycero-D-mannoheptose in the molar ratio of 1:1:1 plus traces of mannose. It consumed 1 mole of sodium metaperiodate per mole of an average anhydroaldose unit and released 0.95 moles of formaldehyde per anhydroheptose unit. Reduction of the oxidized polymer followed by hydrolysis yielded D-glucose, glycerose, glycolaldehyde, and glycerol. Complete fission of the methylated polymer yielded 2,3-di-O-methyl-D-glucuronic acid, 2,4,6,-tri-O-methyl α-D-glucose and 3,4,6,7-tetra-O-methyl D-glycero-D-mannoheptose. Partial hydrolysis of the methylated polymer produced a methylated aldotriouronic acid composed of 1 mole each of 2,3-di-O-methyl-D-glucuronic acid, 2,4,6-tri-O-methyl-D-glucose and 3,4,6,7-tetra-O-methyl D-glycero-D-mannoheptose. A methylated aldobiouronic acid was also produced and was shown to be composed of 2,3-di-O-methyl-D-glucuronic acid and 2,4,6-tri-O-methyl D-glucose.On the basis of these results it is proposed that the polysaccharide is a linear molecule composed of repeating units of D-glucuronic acid, D-glucose, and D-glycero-D-mannoheptose.

Structure of some sulfated sugars isolated after acid hydrolysis of the extracellular polysaccharide of Porphyridium sp., a unicellular red alga

1991 ◽  
Vol 210 ◽  
pp. 349-352 ◽  
Author(s):  
Niculina Lupescu ◽  
Shoshana (Malis) Arad ◽  
Shimona Geresh ◽  
Michael A. Bernstein ◽  
Robert Glaser
Keyword(s):  
Acid Hydrolysis ◽  
Extracellular Polysaccharide ◽  
Red Alga ◽  
Hydrolysis Of

scholarly journals 4-O-(1-carboxyethyl)-l-rhamnose, a second unique acidic sugar found in an extracellular polysaccharide from Butyrivibrio fibrisolvens strain 49

1990 ◽  
Vol 268 (2) ◽  
pp. 281-285 ◽  
Author(s):  
R J Stack ◽  
D Weisleder
Keyword(s):  
Chemical Ionization ◽  
Extracellular Polysaccharide ◽  
Spectroscopic Studies ◽  
Chemical Degradation ◽  
Ionization Mass ◽  
Unknown Compound ◽  
Butyrivibrio Fibrisolvens ◽  
Neutral Sugars ◽  
Acidic Component ◽  
Unknown Structure

Butyrivibrio fibrisolvens strain 49 excretes a polysaccharide that contains D-glucose, D-galactose, 4-O-(1-carboxyethyl)-D-galactose, and an acidic component of previously unknown structure. We report here the identity of the unknown as 4-O-(1-carboxyethyl)-L-rhamnose. The structure of this previously unknown compound was deduced from (1) comprehensive electron-impact and chemical-ionization mass-spectroscopic studies of differentially labelled derivatives prepared from the unknown, (2) 13C-n.m.r. and 1H-n.m.r. studies of purified neutral sugars derived from the unknown and (3) chemical degradation experiments.

scholarly journals Anverenes B–E, New Polyhalogenated Monoterpenes from the Antarctic Red Alga Plocamium cartilagineum

Marine Drugs ◽  
2019 ◽  
Vol 17 (4) ◽  
pp. 230 ◽  
Author(s):  
Andrew J. Shilling ◽  
Jacqueline L. von Salm ◽  
Anthony R. Sanchez ◽  
Younghoon Kee ◽  
Charles D. Amsler ◽  
...  
Keyword(s):  
Chemical Ionization ◽  
Red Alga ◽  
Chemical Ionization Mass Spectrometry ◽  
Ionization Mass ◽  
Negative Chemical Ionization ◽  
Western Antarctic Peninsula ◽  
One Dimensional ◽  
Halogenated Monoterpenes ◽  
The Antarctic ◽  
Plocamium Cartilagineum

The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (2–5) as well as undescribed compounds of the same class, anverenes B–D (6–8). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy and negative chemical ionization mass spectrometry. Compounds 1–9 show moderate cytotoxicity against cervical cancer (HeLa) cells.

A STUDY ON THE LIBERATION OF SUGARS, HEXURONIC ACID, AND HEXOSAMINE FROM BIOLOGICAL MATERIAL

1961 ◽  
Vol 39 (4) ◽  
pp. 671-681 ◽  
Author(s):  
W. Haab ◽  
P. A. Anastassiadis
Keyword(s):  
Hyaluronic Acid ◽  
Hydrochloric Acid ◽  
Biological Material ◽  
Dilute Hydrochloric Acid ◽  
Glucuronic Acid ◽  
Chondroitin Sulphate ◽  
Hydrolytic Cleavage ◽  
Hexuronic Acid ◽  
Polystyrene Resin ◽  
Hydrolysis Of

Sulphonated polystyrene resin suspended in dilute hydrochloric acid and 4 N hydrochloric acid were compared with respect to (a) efficiency as catalysts of hydrolytic cleavage of mucopolysaccharides and (b) rates of destruction of sugars, glucuronic acid, and glucosamine. Mannose, galactose, and glucose were not subject to serious destruction when heated with the resin suspension over a period that was sufficient to effect hydrolysis of mucopolysaccharides and glycoproteins. All these sugars were subject to serious destruction when heated with 4 N hydrochloric acid for a period sufficient to effect hydrolysis of mucopolysaccharides and glycoproteins. Under similar conditions, pentoses were destroyed more rapidly than hexoses but ribose withstood heating with the resin suspension for several hours. Heparin was found to be more resistant to hydrolysis than chondroitin sulphate or hyaluronic acid.

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