Structural components of alginic acid. I. The crystalline structure of poly‐β‐<scp>D</scp>‐mannuronic acid. Results of X‐ray diffraction and polarized infrared studies

Atkins, E. D. T.; Nieduszynski, Ian A.; Mackie, William; Parker, Kate; Smolko, Eduardo E.

doi:10.1002/bip.1973.360120813

Cited by 179 publications

(83 citation statements)

References 16 publications

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“…A D-mannuronate prefers a 3-fold left-handed helix with weak intra-molecular hydrogen bonding between the 3-OH group and the ring oxygen of the adjacent residue of the nonreducing side, whereas a L-guluronate forms stiffer 2-fold screw helical chains through intramolecular hydrogen bonding between the carboxyl group and the 2-OH of the reducing side [31][32][33]. This influences the extent of cross ring fragmentations 2,5 A red and 0,4 A red .…”

Section: Discussionmentioning

confidence: 99%

Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry

Zhang

Zhao

et al. 2006

J. Am. Soc. Mass Spectrom.

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Negative-ion electrospray tandem mass spectrometry (ES-MS/MS) with collision-induced dissociation (CID) is attempted for sequence determination of alginate oligosaccharides, derived from polyanionic alginic acid, polymannuronate, and polyguluronate by partial depolymerization using either alginate lyase or mild acid hydrolysis. Sixteen homo-and hetero-oligomeric fragments were obtained after fractionation by gel-filtration and strong anion exchange high performance liquid chromatography. The product-ion spectra of these alginate oligosaccharides were dominated by intense B-, C-, Y-, and Z-type ions together with 0,2 A-and 2,5 A-ions of lower intensities. Internal mannuronate residues (M) produce weak but specific decarboxylated Z int -ions (Z int Ϫ 44 Da; int: denotes internal), which can be used for distinction of M and a guluronate residue (G) at an internal position. A reducing terminal M or G, although neither gives rise to a specific ion, can be identified by differences in the intensity ratio of fragment ions of the reducing terminal residue [ [2,3]. Infection with the latter opportunistic pathogen seen in cystic fibrosis patients remains a major health concern [4]. Alginate consists of hexuronic acid residues ␤-Dmannuronic acid (M) and ␣-L-guluronic acid (G) with exclusively 1¡4 glycosidic linkages. Along its linear chain, there are homo-oligomeric regions of mannuronate (M-blocks) and of guluronate (G-blocks) as well as hetero-oligomeric regions (MG-blocks) [5,6]. In contrast to algal alginate and alginate of A. vinelandii, the absence of G-blocks or low ratio of G-to M-blocks is characteristic for alginate from most bacteria such as P. aeruginosa. The alginate coat of P. aeruginosa is known to provide protection from immune defence system. Oligomannuronates have been shown to have an inhibitory effect on reactive oxidizing species production [7] from immune cells, whereas oligoguluronates with similar sizes did not exhibit any significant effect [8]. The physical properties of the alginates have also been well documented and can be used as thermally stable cold setting gelling agents in the presence of calcium ions, gelling at far lower concentrations than gelatin. High G content produces strong, brittle gels with good heat stability whereas high M content produces weaker, more-elastic gels with good freeze-thaw behavior. Alginate oligosaccharide fragments and their derivatives have been widely used as releasing agents in the pharmacy [9], as additives in the food industry [10], and as growth-promoters in agriculture [11]. Recently, it has also found important applications in tissue engineering [12].Polyanionic oligosaccharides such as those derived from glycosaminoglycans have attracted considerable interests recently because of the increased awareness of their functional properties. The functional properties of alginates and their oligosaccharide fragments are intimately linked to the composition (M/G ratio) and sequences of the hexuronic acid M and G residues. Methods for identification of oligosacc...

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Section: Discussionmentioning

confidence: 99%

Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry

Zhang

Zhao

et al. 2006

J. Am. Soc. Mass Spectrom.

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“…A conformation adopted under acidic form which would be stabilized by hydrogen bonding. 16 It would correspond perhaps to a helix with a A%, . threefold screw symmetry as described by Palmer and Hartzog17 for sodium pectinates in the solid state.…”

Section: Studiesmentioning

confidence: 99%

Investigation on oligo‐ and polygalacturonic acids by potentiometry and circular dichroism

Ravanat

Rinaudo

1980

Biopolymers

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SynopsisThe potentiometric data concerning the dependence of the apparent pK with the degree of neutralization and the nature of counterions (Na or Ca) of galacturonic oligomers and polymers are discussed. They are characterized by an apparent charge density A,, which predicts their electrostatic behavior. The calculated osmotic coefficients from Katchalsky and Manning's theories are in good agreement with the experimental data obtained by potentiometry. The dependence of the osmotic coefficient (&a) as a function of the polymer concentration is established by potentiometry and interpreted in terms of a multichain aggregation. In addition, it is proven that no Ca2+ is ever fixed in excess of stoichiometry. The dependence of CD spectra obtained under the same conditions as the pK measurements shows analogies between the two sets of results. The CD data, in agreement with W -n m r measurements, suggest that in dilute solutions the polymer adopts two conformations: one (acidic form) which may be represented by threefold screw symmetry and a second (Na or Ca form) which can be related to a twofold screw symmetry. The twofold screw symmetry is known to allow the formation of cooperative "egg-box'' fixation of Ca without conformation change.

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“…The average surface area per group is around 3 nm 2 per site (S. muticum). As a matter of comparison, the length of the disaccharide unit in polymannuronic and polyguluronic acid fibres, determined by X-ray diffraction (Atkins et al, 1973a;Atkins et al, 1973b) is 1.04-0.87 nm.…”

Section: Surface Charge and Permeable Gel Descriptions Of The Ionic Smentioning

confidence: 99%

Surface charge and permeable gel descriptions of the ionic strength influence on proton binding to seaweed biomass

Rey-Castro

Herrero

Vicente

2004

Chemical Speciation & Bioavailability

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Structural components of alginic acid. I. The crystalline structure of poly‐β‐D‐mannuronic acid. Results of X‐ray diffraction and polarized infrared studies

Cited by 179 publications

References 16 publications

Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry

Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry

Investigation on oligo‐ and polygalacturonic acids by potentiometry and circular dichroism

Surface charge and permeable gel descriptions of the ionic strength influence on proton binding to seaweed biomass

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