Novel carbonyl-group-containing dextran synthesis by pyranose-2-oxidase and dextransucrase

Seto, Hirokazu; Kawakita, Hidetaka; Ohto, Keisuke; Harada, Hiroyuki; Inoue, Katsutoshi

doi:10.1016/j.carres.2008.06.027

Cited by 10 publications

(7 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The slope of 1.2 is slightly lower than that of 1.4 reported in previous study (Morris et al, 1981). The lower slope of keto-dextran is probably due to the conformation shrunken by intra-molecular interaction of carbonyl group and the branched structure of keto-dextran compared with dextran (Seto et al, 2008).…”

Section: Rheological Properties Of Dextran and Keto-dextran In The DIcontrasting

confidence: 72%

“…Synthesis of keto-dextran was carried out by combination of the three enzymatic reactions (P2Ox, catalase, and DSase) as previous report (Seto et al, 2008). To control the molecular weight of dextran and keto-dextran, the polysaccharide solutions were treated by ultrasonication using an ultrasonic cleaner (Branson 3510J-DTH, Oscillating frequency; 42 kHz, ultrasonic wave; 130 W) for 12 h at 50°C.…”

Section: Preparation Of Sugar Solutionsmentioning

confidence: 99%

“…We have previously reported that the synthesis of keto-dextran containing high-density carbonyl groups, in which carbonyl groups were prospectively introduced to sucrose as a substrate, subsequently keto-dextran was enzymatically polymerized from the substrate contained carbonyl group (Seto, Kawakita, Ohto, Harada, & Inoue, 2008). Carbonyl groups of keto-dextran create novel Hbonding with water molecules and hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Rheological properties of keto-sugars with high-density carbonyl groups

Seto

Ohto

Harada

et al. 2010

Carbohydrate Polymers

Self Cite

View full text Add to dashboard Cite

Section: Rheological Properties Of Dextran and Keto-dextran In The DIcontrasting

confidence: 72%

Section: Preparation Of Sugar Solutionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Rheological properties of keto-sugars with high-density carbonyl groups

Seto

Ohto

Harada

et al. 2010

Carbohydrate Polymers

Self Cite

View full text Add to dashboard Cite

“…activity) as substrates (Table 7 , entries 9, 13 and 19) (Danneel et al 1993 ; Freimund et al 1998 ; Takakura and Kuwata 2003 ). Moreover, P2O was used as a biocatalyst for the C 2 oxidation of disaccharides to obtain 2-keto-aldopyranose intermediates (Leitner et al 2001 ) and the di-sugar d -sucrose (Table 7 , entry 11) was fully converted by P2O in a multistep process (Seto et al 2008 ).…”

Section: Sugar-related Alcoholsmentioning

confidence: 99%

The substrate tolerance of alcohol oxidases

Pickl

Fuchs

Glueck

et al. 2015

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

Alcohols are a rich source of compounds from renewable sources, but they have to be activated in order to allow the modification of their carbon backbone. The latter can be achieved via oxidation to the corresponding aldehydes or ketones. As an alternative to (thermodynamically disfavoured) nicotinamide-dependent alcohol dehydrogenases, alcohol oxidases make use of molecular oxygen but their application is under-represented in synthetic biotransformations. In this review, the mechanism of copper-containing and flavoprotein alcohol oxidases is discussed in view of their ability to accept electronically activated or non-activated alcohols and their propensity towards over-oxidation of aldehydes yielding carboxylic acids. In order to facilitate the selection of the optimal enzyme for a given biocatalytic application, the substrate tolerance of alcohol oxidases is compiled and discussed: Substrates are classified into groups (non-activated prim- and sec-alcohols; activated allylic, cinnamic and benzylic alcohols; hydroxy acids; sugar alcohols; nucleotide alcohols; sterols) together with suitable alcohol oxidases, their microbial source, relative activities and (stereo)selectivities.Electronic supplementary materialThe online version of this article (doi:10.1007/s00253-015-6699-6) contains supplementary material, which is available to authorized users.

show abstract

“…However, the bioconversion of D-glucose and other carbohydrates in the presence of glucose 2-oxidase and catalase into their corresponding keto sugars is very slow and timeconsuming at atmospheric pressure (1 bar) and at room temperature (23°C) [9,10]. Moreover, glucose 2-oxidase activity is highly unstable [11,12], and there is a great need to stabilize the enzyme activity by several ways such as by protein engineering and by immobilization in a suitable support [13].…”

Section: Introductionmentioning

confidence: 99%

Bioconversion of d-glucose into d-glucosone by Glucose 2-oxidase from Coriolus versicolor at Moderate Pressures

Karmali

Coelho

2010

Appl Biochem Biotechnol

View full text Add to dashboard Cite

Abstract:The immobilized glucose 2-oxidase (pyranose oxidase, pyranose:oxygen-2-oxidoreductase, EC 1.1.3.10) from Coriolus versicolor was used to convert D-glucose into D-glucosone at moderate pressures, up to 150 bar, with compressed air in a modified commercial batch reactor. Several parameters affecting biocatalysis at moderate pressures were investigated as follows: pressure, different forms of immobilized biocatalysts, glucose concentration, pH, temperature and the presence of catalase. Glucose 2-oxidase (GOX2) was purified by immobilized metal affinity chromatography on epoxy-activated Sepharose 6B-IDA-Cu(II) column at pH 6.0. Purified enzyme and catalase were immobilized into a polyethersulfone (PES) membrane in the presence of glutaraldehyde and gelatin. Enhancement of the bioconversion of D-glucose was done by the pressure since an increase in the pressure with compressed air increases the conversion rates. The optimum temperature and pH for bioconversion of D-glucose were found to be 62 degrees C and pH 6.0, respectively and the activation energy (E(a)) was 28.01 kJ mol(-1). The apparent kinetic constants (V(max)' K(m)', K(cat)' and K(cat)/K(m)') for this bioconversion were 2.27 U mg(-1) protein, 11.15 mM, 8.33 s(-1) and 747.38 s(-1) M(-1), respectively. The immobilized biomass of C. versicolor as well as crude extract containing GOX2 activity were also useful for bioconversion of D-glucose at 65 bar with a yield of 69.9 +/-3.8% and 91.3 +/-1.2%, respectively. The immobilized enzyme was apparently stable for several months without any significant loss of enzyme activity. On the other hand, this immobilized enzyme was also stable at moderate pressures, since such pressures did not affect significantly the enzyme activity. (C)

show abstract

Novel carbonyl-group-containing dextran synthesis by pyranose-2-oxidase and dextransucrase

Cited by 10 publications

References 31 publications

Rheological properties of keto-sugars with high-density carbonyl groups

Rheological properties of keto-sugars with high-density carbonyl groups

The substrate tolerance of alcohol oxidases

Bioconversion of d-glucose into d-glucosone by Glucose 2-oxidase from Coriolus versicolor at Moderate Pressures

Contact Info

Product

Resources

About