Structural studies on κ-carrageenan derived oligosaccharides

Yu, Guangli; Guan, Huashi; Ioanoviciu, Alexandra; Sikkander, Sulthan A.; Thanawiroon, Charuwan; Tobacman, Joanne K.; Toida, Toshihiko; Linhardt, Robert J.

doi:10.1016/s0008-6215(02)00009-5

Cited by 113 publications

(60 citation statements)

References 21 publications

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“…Hydrolysis Products Analysis of AgaB-The dynamics of hydrolysis of agarose (0.25%) with AgaB (0.01 M) at 40°C was traced for up to 24 h. An aliquot of hydrolysis product was taken out at different times and analyzed using fluorophore-assisted carbohydrate electrophoresis (FACE) (37).…”

Section: Methodsmentioning

confidence: 99%

Molecular Cloning and Characterization of a Novel β-Agarase, AgaB, from Marine Pseudoalteromonas sp. CY24

Shi

et al. 2007

Journal of Biological Chemistry

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Agarases are generally classified into glycoside hydrolase families 16, 50, and 86 and are found to degrade agarose to frequently generate neoagarobiose, neoagarotetraose, or neoagarohexaose as the main products. In this study we have cloned a novel endo-type ␤-agarase gene, agaB, from marine Pseudoalteromonas sp. CY24. The novel agarase encoded by agaB gene has no significant sequence similarity with any known proteins including all glycoside hydrolases. It degrades agarose to generate neoagarooctaose and neoagarodecaose as the main end products. Based on the analyses of enzymatic kinetics and degradation patterns of different oligosaccharides, the agarase AgaB appears to have a large substrate binding cleft that accommodates 12 sugar units, with 8 sugar units toward the reducing end spanning subsites ؉1 to ؉8 and 4 sugar units toward the non-reducing end spanning subsites ؊4 to ؊1, and enzymatic cleavage taking place between subsites ؊1 and ؉1. In addition, 1 H NMR analysis shows that this enzyme hydrolyzes the glycosidic bond with inversion of anomeric configuration, in contrast to other known agarases that are retaining. Altogether, AgaB is structurally and functionally different from other known agarases and appears to represent a new family of glycoside hydrolase.

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Section: Methodsmentioning

confidence: 99%

Molecular Cloning and Characterization of a Novel β-Agarase, AgaB, from Marine Pseudoalteromonas sp. CY24

Shi

et al. 2007

Journal of Biological Chemistry

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“…Galactan oligosaccharides can be obtained through partial acid (Yu et al, 2002;Gonçalves et al, 2010;Ciancia et al, 2005) or enzymatic hydrolysis (Guibet et al, 2006;Young et al, 1978;Rochas et al, 1994). Usually, the partial acid hydrolysis methods (Figure 1) promote the specifi c cleavage of 3,6-anhydro-α-galactosidic bonds to produce the reducing di-or tetrasaccharides 2 and 4, containing the unusual anhydro galactose in hydrated aldehyde form as the terminal unit.…”

Section: Introductionmentioning

confidence: 99%

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

Ducatti¹,

Colodi²,

Gonçalves³

et al. 2011

Rev. bras. farmacogn.

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Agaro-and carra-oligosaccharides were produced by partial acid hydrolysis of commercial agarose and kappa-carrageenan. Di-and tetrasaccharides were purified by gel filtration chromatography and characterized by NMR (1D and 2D) spectroscopy and ESIMS. The following oligosaccharides were obtained: agarobiose, agarotetraose, kappa-carrabiose and kappa-carratetraose. Agarobiose and agarotetraose were used as standards to develop a high performance size exclusion chromatography (HPSEC) method which was utilized to study the hydrolysis rate of agarose and oligosaccharide production. Six hours of hydrolysis (0.1 M TFA, 65 o C) produced mainly di-and tetrasaccharides. The methodology for oligosaccharide production and evaluation developed in the present work shows good potential for the production of bioactive oligosaccharides. Keywords:agaro-oligosaccharides carra-oligosaccharides partial acid hydrolysis 3,6-anhydro-galactose agarose kappa-carrageenan

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“…15) Similar results, including the formation of even-numbered oligosaccharides from red algal galactans, have been reported by several other researchers. 16,17) On the other hand, Yu 18) and Yang et al 19) reported recently the formation of odd-numbered oligosaccharides by mild acid hydrolysis of -carrageenan and both -carrageenan and agarose, respectively. In their studies, residues at the reducing end were determined to be Gal, not AG.…”

Section: Resultsmentioning

confidence: 99%

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

Hama

Tsuneoka

Morita

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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Here we report a simple method for the structural analysis of red algal galactan containing 3,6-anhydrogalactose. Structural heterogeneity in the galactan was demonstrated by this method. For selective hydrolysis of 3,6-anhydrogalactosidic linkages in the galactan, conditions for reductive mild acid hydrolysis were examined by characterizing the resulting oligosaccharide alditols by anhydrous mercaptolysis. Residues other than alditols at the reducing ends, including labile 3,6-anhydrogalactose, were liberated quantitatively as diethyl dithioacetal derivatives, whereas alditols at the reducing ends were not derivatized and were liberated as alditols intact. The liberated sugars were then separated and measured quantitatively by gas-liquid chromatography. Heating of agarose in reductive hydrolysis with 0.3 M trifluoroacetic acid in the presence of an acid-stable reducing agent, 4-methyl morpholine borane, at 80 C for 90 min and for 90 C for 45 min was found to be optimum for the selective hydrolysis of 3,6-anhydrogalactosidic bonds, without detectable cleavage of other glycosidic bonds.Key words: 3,6-anhydrogalactose; algal galactan; heterogeneity; mercaptolysis; reductive hydrolysis Various biological activities have been found in marine algal polysaccharides.1-3) However, since algal polysaccharides in nature are generally heterogeneous in size and composition, the structure-activity relationships of these saccharides are not fully established yet.Red algal galactans such as agar, carrageenans, and porphyran contain 3,6-anhydrogalactose (AG) as a major component monosaccharide. 4) Since AG is easily destroyed by harsh acidic conditions such as acid hydrolysis and methanolysis, which are generally used in compositional and structural analysis of polysaccharides, the details of the structure of these algal galactans remain to be elucidated. Stevenson and Furneaux5) reported a double-hydrolysis procedure in which mild acid hydrolysis was employed to cleave only 3,6-anhydrogalactosidic linkages, followed by reduction with sodium borohydride. The resulting oligosaccharide alditols with 3,6-anhydrogalactitol at the reducing ends were fully hydrolyzed for compositional analysis by gas-liquid chromatography (GLC). They also developed a reductive hydrolysis procedure in which mild acid hydrolysis is carried out in the presence of an acid-stable reducing agent, 4-methyl morpholine borane (MMB), to obtain oligosaccharide alditols with 3,6-anhydrogalactitol at the reducing ends.5) Since then, these methods have been modified by several other groups.6-8) However, the degree of hydrolysis of the 3,6-anhydrogalactosidic bonds in the galactans was evaluated by determining the resulting AG-ol, because AG, unlike AG-ol, cannot be measured directly by these methods. Therefore, the behavior of the remaining AG residues during the reaction period remains substantially unknown.We have reported a method for the determination of component monosaccharides of red algal galactans by which all the component sugars including AG were libera...

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Structural studies on κ-carrageenan derived oligosaccharides

Cited by 113 publications

References 21 publications

Molecular Cloning and Characterization of a Novel β-Agarase, AgaB, from Marine Pseudoalteromonas sp. CY24

Molecular Cloning and Characterization of a Novel β-Agarase, AgaB, from Marine Pseudoalteromonas sp. CY24

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

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