A Novel Open-Chain Nononic Acid Linked by an Ether Bond to Glucose as a Polysaccharide Constituent

Faber, Elisabeth J.; Kuik, J. Albert van; Halkes, Koen M.; Kamerling, Johannis P.; Vliegenthart, Johannes F.G.

doi:10.1002/1521-3765(20021004)8:19<4498::aid-chem4498>3.0.co;2-0

Cited by 4 publications

(11 citation statements)

References 36 publications

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“…GLC monosaccharide analysis, including absolute configuration determination, of the native EPS (n‐EPS) showed the presence of d ‐Gal, d ‐Glc, d ‐Rib, and d ‐GalNAc in a molar ratio of 2 : 1 : 1 : 1. In addition, GLC peaks were observed originating from a novel constituent, 6‐ O‐ (3′,9′‐dideoxy‐ d ‐ threo ‐ d ‐ altro ‐nononic acid‐2′‐yl)‐ d ‐glucopyranose [10]. The molar ratio of this constituent in terms of peak areas was 0.7 compared to Glc.…”

Section: Isolation Purification and Composition Of The Polysaccharidementioning

confidence: 99%

“…Methylation analysis of n‐EPS revealed, besides the occurrence of a product stemming from the novel constituent, the presence of 4‐substituted Glc p , 4‐substituted Gal p , 4‐substituted Gal p NAc, and 2‐substituted Rib f (for evidence of the pyranose ring forms, see NMR analysis) in a molar ratio of 1.0 : 1.7 : 0.6 : 0.7. Methylation analysis of n‐EPS after carboxyl‐reduction (cr‐EPS) yielded also the substitution pattern of the novel constituent: 7′‐substituted 6‐ O‐ (3′,9′‐dideoxy‐nonitol‐2′‐yl)‐Glc p [10]. Based on these results, a linear heteropolysaccharide is indicated.…”

Section: Isolation Purification and Composition Of The Polysaccharidementioning

confidence: 99%

“…In the ES spectrum a sodium‐cationized [M + Na] + pseudomolecular ion was observed at m/z 1204 corresponding to Hex 3 Pent 1 Sug 1 anhydroHex 1 ‐ol‐ 1‐d . Furthermore, a [M + Na] + ion was present at m/z 1186, arising from the loss of water due to the formation of an intraresidual lactone in the nononic acid part of Sug [10]. The tandem mass spectrum obtained on collision activation of the pseudomolecular ion at m/z 1204 (Fig.…”

Section: De‐n‐acetylation and Deamination Of The Native Polysaccharidementioning

confidence: 99%

“…From the assigned 1 H chemical shifts it was clear that A , C and E are Gal p (NAc) residues since their downfield chemical shift of H‐4 are characteristic for galacto ‐hexopyranose residues [23]. Residue B was assigned as Glc p by the characteristic upfield chemical shift of B H‐2 [23], and residue D as Sug [10]. Finally, residue F could be assigned as the Rib f residue by its spin system, which is characteristic for this pentose residue [24].…”

Section: D Nmr Spectroscopy Of the Native Polysaccharidementioning

confidence: 99%

“…Recently [10], we reported for the EPS produced by S. thermophilus 8S the occurrence of a Glc residue etherified at O‐6 with a novel open chain nononic acid, i.e. 6‐ O‐ (3′,9′‐dideoxy‐ d ‐ threo ‐ d ‐ altro ‐nononic acid‐2′‐yl)‐ d ‐glucopyranose.…”

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Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid

Faber

Haaster

Kamerling

et al. 2002

European Journal of Biochemistry

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The exopolysaccharide produced by Streptococcus thermophilus 8S in reconstituted skimmed milk is a heteropolysaccharide containing D-galactose, D-glucose, D-ribose, and N-acetyl-D-galactosamine in a molar ratio of 2 : 1 : 1 : 1.Furthermore, the polysaccharide contains one equivalent of a novel open chain nononic acid constituent, 3,9-dideoxy-Dthreo-D-altro-nononic acid, ether-linked via C-2 to C-6 of an additional D-glucose per repeating unit. Methylation analysis and 1D/2D NMR studies ( 1 H and 13 C) performed on the native polysaccharide, and mass spectrometric and NMR analyses of the oligosaccharide obtained from the polysaccharide by de-N-acetylation followed by deamination and reduction demonstrated the ÔheptaÕsaccharide repeating unit to be:Keywords: exopolysaccharide; lactic acid bacteria; nononic acid; Streptococcus thermophilus; structural analysis.Microbial exopolysaccharides (EPSs) are employed in the food industry as viscosifying, stabilizing, emulsifying and gelling agents [1]. The texturizing properties of EPSs in fermented dairy products [2] in combination with the GRAS (generally recognized as safe) status of EPS-producing lactic acid bacteria, make these EPSs of interest for the food industry. To understand the relationship between the structure of EPSs and their physical properties, structural studies have been performed on EPSs produced by various species of the Lactobacillus, Lactococcus, and Streptococcus genera ([3,4], and references cited therein).The lactic acid bacterium Streptococcus thermophilus is used in combination with other lactic acid bacteria like Lactobacillus delbrueckii ssp. bulgaricus as starter culture for fermentations in dairy industry. In the last decade, the primary structure of the EPSs secreted by seven S. thermophilus strains [5][6][7][8][9] were elucidated. A number of the EPSs are structurally related polysaccharides and include the EPSs produced by S. thermophilus Sfi12 Recently [10], we reported for the EPS produced by S. thermophilus 8S the occurrence of a Glc residue etherified at O-6 with a novel open chain nononic acid, i.e. 6-O-(3¢,9¢-dideoxy-D-threo-D-altro-nononic acid-2¢-yl)-D-glucopyranose. Here, we report the complete structure of this EPS.

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Section: Isolation Purification and Composition Of The Polysaccharidementioning

confidence: 99%

Section: Isolation Purification and Composition Of The Polysaccharidementioning

confidence: 99%

Section: De‐n‐acetylation and Deamination Of The Native Polysaccharidementioning

confidence: 99%

Section: D Nmr Spectroscopy Of the Native Polysaccharidementioning

confidence: 99%

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confidence: 99%

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Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid

Faber

Haaster

Kamerling

et al. 2002

European Journal of Biochemistry

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Harvey¹

2008

Mass Spectrometry Reviews

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This review is the second update of the original review on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates that was published in 1999. It covers fundamental aspects of the technique as applied to carbohydrates, fragmentation of carbohydrates, studies of specific carbohydrate types such as those from plant cell walls and those attached to proteins and lipids, studies of glycosyl-transferases and glycosidases, and studies where MALDI has been used to monitor products of chemical synthesis. Use of the technique shows a steady annual increase at the expense of older techniques such as FAB. There is an increasing emphasis on its use for examination of biological systems rather than on studies of fundamental aspects and method development and this is reflected by much of the work on applications appearing in tabular form.

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Structural analysis of the exopolysaccharide produced by Streptococcus thermophilus ST1 solely by NMR spectroscopy

et al. 2010

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The use of lactic acid bacteria in fermentation of milk results in favorable physical and rheological properties due to in situ exopolysaccharide (EPS) production. The EPS from S. thermophilus ST1 produces highly viscous aqueous solutions and its structure has been investigated by NMR spectroscopy. Notably, all aspects of the elucidation of its primary structure including component analysis and absolute configuration of the constituent monosaccharides were carried out by NMR spectroscopy. An array of techniques was utilized including, inter alia, PANSY and NOESY-HSQC TILT experiments. The EPS is composed of hexasaccharide repeating units with the following structure: --> 3)[alpha-D-Glcp-(1 --> 4)]-beta-D-Galp-(1 --> 4)-beta-D-Glcp-(1 --> 4)[beta-D-Galf-(1 --> 6)]-beta-D-Glcp-(1 --> 6)-beta-D-Glcp-(1 -->, in which the residues in square brackets are terminal groups substituting backbone sugar residues that consequently are branch-points in the repeating unit of the polymer. Thus, the EPS consists of a backbone of four sugar residues with two terminal sugar residues making up two side-chains of the repeating unit. The molecular mass of the polymer was determined using translational diffusion experiments which resulted in Mw = 62 kDa, corresponding to 64 repeating units in the EPS.

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A Novel Open-Chain Nononic Acid Linked by an Ether Bond to Glucose as a Polysaccharide Constituent

Cited by 4 publications

References 36 publications

Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid

Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 2001–2002

Structural analysis of the exopolysaccharide produced by Streptococcus thermophilus ST1 solely by NMR spectroscopy

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