Photolytic depolymerization of alginate

Burana-osot, Jankana; Hosoyama, Saori; Nagamoto, Yuzu; Suzuki, Sho; Linhardt, Robert J.; Toida, Toshihiko

doi:10.1016/j.carres.2009.06.027

Cited by 52 publications

(32 citation statements)

References 31 publications

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“…Several methods have been used to adjust the molecular weight and G/M ratio, including acid hydrolysis (Haug, Myklestad, Larsen, & Smidsrod, 1967), base hydrolysis (Rigouin, Delbarre, Sinquin, Colliec-Jouault, & Dion, 2009), enzymatic depolymerisation (Kim et al, 2012), photolytic depolymerisation (Burana-Osot et al, 2009), and hydrothermal conditions (Aida, Yamagata, Watanabe, & Smith, 2010). Traditional methods use organic solvents such as ethanol, methanol, or hexane during the extraction process (Demirel, Yilmaz-Koz, Karabay-Yavagoslu, Ozdemir, & Sukatar, 2009;Osman, Abushady, & Elshobary, 2010).…”

Section: Introductionmentioning

confidence: 99%

Production of monosaccharides and bio-active compounds derived from marine polysaccharides using subcritical water hydrolysis

2015

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Section: Introductionmentioning

confidence: 99%

Production of monosaccharides and bio-active compounds derived from marine polysaccharides using subcritical water hydrolysis

2015

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“…In previous studies, we have reported the depolymerization of simple, nonsulfated polysaccharides, sodium alginate, pectin and heparosan using a photochemical reaction relying on TiO 2 catalyst (23-25). The controlled depolymerization of sodium alginate, pectin and heparosan were successfully accomplished and the resulting products maintained the intact core structure of alginate, pectin and heparosan.…”

Section: Introductionmentioning

confidence: 99%

Photochemical preparation of a novel low molecular weight heparin

Higashi

Hosoyama

Ohno

et al. 2012

Carbohydrate Polymers

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Commercial low molecular weight heparins (LMWHs) are prepared by several methods including peroxidative cleavage, nitrous acid cleavage, chemical ß-elimination, and enzymatic β-elimination. The disadvantages of these methods are that strong reaction conditions or harsh chemicals are used and these can result in decomposition or modification of saccharide units within the polysaccharide backbone. These side-reactions reduce product quality and yield. Here we show the partial photolysis of unfractionated heparin can be performed in distillated water using titanium dioxide (TiO2). TiO2 is a catalyst that can be easily removed by centrifugation or filtration after the photochemical reaction takes place, resulting in highly pure products. The anticoagulant activity of photodegraded LMWH (pLMWH) is comparable to the most common commercially available LMWHs (i.e., Enoxaparin and Dalteparin). 1H NMR spectra obtained show that pLMWH maintains the same core structure as unfractionated heparin. This photochemical reaction was investigated using liquid chromatography/mass spectrometry (LC/MS) and unlike other processes commonly used to prepare LMWHs, photochemically preparation affords polysaccharide chains of reduced length having both odd and even of saccharide residues.

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“…6b), furthermore, the characteristic signals at 4.47, 4.78, and 5.03 ppm assignable to H-5 of G in GG-block, H-1 of M, and H-1 of G, respectively, are detected, which are also observed in that of a commercial alginic acid sample (Fig. 6a) [35]. These analytical data support that the alginate component present in the composite has successfully been isolated by the alkaline treatment.…”

Section: Resultsmentioning

confidence: 57%