13C-nuclear magnetic resonance spectra of compounds containing β-D-fructofuranosyl groups or residues

Seymour, Fred R.; Knapp, Roger D.; Zweig, J. E.; Bishop, Stephen H.

doi:10.1016/s0008-6215(00)83923-3

Cited by 60 publications

(9 citation statements)

References 19 publications

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“…The fact that the quaternary anomeric carbons have a greater intensity (height) than the other resonances is interesting and appears to be a common phenomena in fructofuranose polymers such as levan and inulin [20,21].…”

Section: Discussionmentioning

confidence: 99%

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

Barrow¹,

Collins²,

Rogers³

et al. 1984

Eur J Biochem

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A novel polysaccharide has been observed in uivo by 13C nuclear magnetic resonance (NMR) spectroscopy of the gram-negative bacterium, Zymomonas mobilis. The polysaccharide, which was not removed from the Zmobilis cell by washing with 0.86 % saline, was extracted by mild acid treatment. The structure was elucidated by a combination of NMR techniques, including proton and proton-carbon two-dimensional methods. The structure was determined to be -a-fructofuranosyl-(2-1)-~-fructofuranosyl-(2-6)-. The polysaccharide is unlike levan, a p-(2-6)-fructose polymer which is produced by many bacteria, including Z.mobilis, when grown on sucrose. The polysaccharide isolated here is produced by cells cultured on glucose, fructose or sucrose.Polyfructosides are generally subdivided into two main classes : levans, in which the main interglycoside linkage is p(2 -6), and inulin, in which the main linkage is p(2 -1) [1]. Both inulin and levans are widely distributed throughout the plant kingdom, where they occur as both linear and branched polymers of comparatively low molecular mass and usually contain a small porportion of glucose in addition to fructose.Microbial polyfructosides are generally of the levan type. Levan is produced by both gram-positive and gram-negative bacteria [2] including Zymomonas mobilis. Z . mobilis is a gramnegative bacterium which can ferment only glucose, fructose and sucrose to ethanol anaerobically via the EntnerDoudoroff pathway. Growth on sucrose results in the synthesis of levan while in the absence of sucrose no levan production occurs. The levan produced by Z . mobilis has been shown to be typical of the bacterial levans containing only fructose in the furanose ring form, linked p(2 -6) with p(2 -1) branch points and a very high molecular mass (approximately 10 MDa) [3].The novel polyfructoside described here has been isolated from Z . mobilis cells grown on glucose and has been found to have a different structure to that of levan and a lower molecular mass. MATERIALS AND METHODS Ma terialsSephacryl 200 was obtained from Pharmacia ; the anionexchange resin, AG3-X4A, was obtained from Bio-Rad. D 2 0 ( 2 99.75 % D) was obtained from the Australian Atomic Energy Commission, Lucas Heights. All other reagents were analytical reagent grade.

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Section: Discussionmentioning

confidence: 99%

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

Barrow¹,

Collins²,

Rogers³

et al. 1984

Eur J Biochem

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“…13 C NMR has often been used to distinguish linear and branched levans from plants or bacteria [45,52]. Intense and sharp signals in linear levan and weak C3 signals downfield from the major C3 signal, or the presence of minor peaks upfield of C6 in branched molecule are referred to as the key features of the spectra [53,54]. Furthermore, no branching was observed in the 13 C NMR spectra of levans from acetic acid bacteria or levan from P. bovis BD352 [5,48].…”

Section: Evidence Of Branching Based On Nmr Spectramentioning

confidence: 99%

Production of levan by Bacillus licheniformis NS032 in sugar beet molasses-based medium

Gojgić-Cvijović

Jakovljević

Lončarević

et al. 2019

International Journal of Biological Macromolecules

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The production of levan by Bacillus licheniformis NS032 in a medium based on sugar beet molasses was studied. High polysaccharide yields were produced by using diluted molasses (100-140 g/L of total sugars) with the addition of commercial sucrose up to 200 g/L of total sugars, as well as K 2 HPO 4. A levan yield of 53.2 g/L was obtained on a medium optimized by response surface methodology, containing 62.6% of sugar originating from molasses, and 4.66 g/L of phosphate, with initial pH value of 7.2. In comparison to the media with 200 and 400 g /L sucrose, in the molasses optimized medium, the observed bacterial growth was faster, while the maximum

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“…oligosaccharides, these techniques are substantially less sensitive. NMR, however, represents a sensitive technique for examining isomeric mixtures of saccharides such as these, and data have been reported for levans and inulin (15), as well as for a number of other fructofuranosyl containing saccharides (4,9,22,23,27). In a previous paper (1 1), we reported an evaluation of this technique using A. officinalis L. root extracts as the source of the saccharides, and have assigned the anomeric carbon and proton signals for both 1-kestose and neokestose.…”

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Detection of Kestoses and Kestose-Related Oligosaccharides in Extracts of Festuca arundinacea, Dactylis glomerata L., and Asparagus officinalis L. Root Cultures and Invertase by ¹³C and ¹H Nuclear Magnetic Resonance Spectroscopy

Forsythe

Feather²,

Gracz³

et al. 1990

Plant Physiol.

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A previous study (KL Forsythe, MS Feather [1989] CarbohydrRes 185: 315-319) showed that 13C nuclear magnetic resonance spectroscopy can be used to detect and identify mixtures of 1-kestose and neokestose after conversion to the acetate derivatives. In this study, unequivocal assignments are made for the anomeric carbon and proton signals for the above two trisaccharide acetates as well as for 6-kestose hendecaacetate and for nystose tetradecaacetate (a 1-kestose-derived tetrasaccharide). A number of oligosaccharide fractions were isolated from several plant species, converted to the acetates, and nuclear magnetic resonance spectra obtained. Using the above reference data, the following information was obtained. The trisaccharide fraction from Dactylis glomerata L. stem tissue and Asparagus officinalis L. roots contain both 1-kestose and neokestose, and the tetrasaccharide fractions contain three components, one of which is nystose. Penta-and hexasaccharide acetates were also isolated from A. officinalis L. roots and were found to contain, respectively, four and at least five components. All components of both of the above species appear to contain a kestose residue and to be produced by the sequential addition of fructofuranosyl units to these. The trisaccharide fraction from Festuca arundinacea is complex, and contains at least five different components, two of which appear to be 1-kestose and neokestose.

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13C-nuclear magnetic resonance spectra of compounds containing β-D-fructofuranosyl groups or residues

Cited by 60 publications

References 19 publications

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

Production of levan by Bacillus licheniformis NS032 in sugar beet molasses-based medium

Detection of Kestoses and Kestose-Related Oligosaccharides in Extracts of Festuca arundinacea, Dactylis glomerata L., and Asparagus officinalis L. Root Cultures and Invertase by ¹³C and ¹H Nuclear Magnetic Resonance Spectroscopy

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13C-nuclear magnetic resonance spectra of compounds containing β-D-fructofuranosyl groups or residues

Cited by 60 publications

References 19 publications

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

The structure of a novel polysaccharide isolated from Zymomonas mobilis determined by nuclear magnetic resonance spectroscopy

Production of levan by Bacillus licheniformis NS032 in sugar beet molasses-based medium

Detection of Kestoses and Kestose-Related Oligosaccharides in Extracts of Festuca arundinacea, Dactylis glomerata L., and Asparagus officinalis L. Root Cultures and Invertase by 13C and 1H Nuclear Magnetic Resonance Spectroscopy

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Detection of Kestoses and Kestose-Related Oligosaccharides in Extracts of Festuca arundinacea, Dactylis glomerata L., and Asparagus officinalis L. Root Cultures and Invertase by ¹³C and ¹H Nuclear Magnetic Resonance Spectroscopy