Synthesis of cellobiose-containing oligosaccharides by intermolecular transglucosylation of cyclodextrin glycosyltransferase from Paenibacillus sp. A11

Wongsangwattana, Wannapa; Kaulpiboon, Jarunee; K, Ito; Pongsawasdi, Piamsook

doi:10.1016/j.procbio.2010.02.024

Cited by 11 publications

(8 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The K m and k cat / K m of Paenibacillus sp. A11 CGTase with maltose as the acceptor are 6.2 × 10 –3 M and 1.2 × 10 5 M –1 min –1 , respectively . In contrast, the K m and k cat / K m of Paenibacillus macerans CGTase with l -AA as the acceptor are 2.55 × 10 –2 M and 3.77 M –1 h –1 , respectively .…”

Section: Introductionmentioning

confidence: 92%

See 1 more Smart Citation

Enhanced 2-O-α-d-Glucopyranosyl-l-ascorbic Acid Synthesis through Iterative Saturation Mutagenesis of Acceptor Subsite Residues in Bacillus stearothermophilus NO2 Cyclodextrin Glycosyltransferase

Tao

Wang

et al. 2018

J. Agric. Food Chem.

View full text Add to dashboard Cite

Low synthesis yields of the l-ascorbic acid (l-AA) derivative 2- O-α-d-glucopyranosyl-l-ascorbic acid (AA-2G) limit its application in the food industry. In this work, the AA-2G synthesis yield of Bacillus stearothermophilus NO2 cyclodextrin glycosyltransferase (CGTase) was improved. Nine residues within 10 Å of the catalytic residue Glu displaying ≤30% conservation and located in the acceptor subsite were selected for iterative saturation mutagenesis. The best mutant, K228R/M230L, produced a higher AA-2G yield with maltodextrin as the glucosyl donor than that produced by its parent wild-type. The l-AA K values of the mutant K228R/M230L decreased by 35%, whereas the k/ K increased by 2.69-fold. Kinetic analysis indicated that K228R/M230L displayed enhanced l-AA specificity. These results demonstrate that acceptor subsite residues play an important role in acceptor substrate specificity. Mutant K228R/M230L afforded the highest AA-2G concentration (211 g L, 624 mM) reported to date after optimization of the reaction conditions.

show abstract

Section: Introductionmentioning

confidence: 92%

“…The K m and k cat / K m of Paenibacillus sp. A11 CGTase with glucose as the acceptor are 6.1 × 10 –3 M and 4.8 × 10 5 M –1 min –1 , respectively . The K m and k cat / K m of Paenibacillus sp.…”

Section: Introductionmentioning

confidence: 99%

Enhanced 2-O-α-d-Glucopyranosyl-l-ascorbic Acid Synthesis through Iterative Saturation Mutagenesis of Acceptor Subsite Residues in Bacillus stearothermophilus NO2 Cyclodextrin Glycosyltransferase

Tao

Wang

et al. 2018

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The results also showed that the relative coupling activity of polyol isomer molecules such as sorbitol-mannitol and xylitol-arabitol isomers were almost equal. Few studies on polyol-acceptor specificity of CGTase have been reported; these have included D- and L-saccharide, alkyl glycoside, flavonoid and alcohol acceptors [ 22 , 27 , 35 ]. Kim et al [ 7 ] reported the synthesis of glucosyl-sugar alcohols, mainly glucosyl-maltitol, using various transglycosylating enzymes including B. macerans CGTase (Amano Pharmaceutical Co., Ltd., Nagoya, Japan).…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Maltitol and Its Inhibitory Effect on the Growth of Streptococcus mutans DMST 18777

2022

Self Cite

View full text Add to dashboard Cite

This study aimed to synthesize maltitol using recombinant CGTase from Bacillus circulans A11 with β-cyclodextrin (β-CD) and sorbitol as a glucosyl donor and acceptor, respectively, and assess its antibacterial activity. Optimal conditions for producing the highest yield, 25.0% (w/w), were incubation of 1% (w/v) β-CD and sorbitol with 400 U/mL of CGTase in 20 mM phosphate buffer at pH 6.0 and 50 °C for 72 h. Subsequently, maltitol underwent large-scale production and was purified by HPLC. By mass spectrometry, the molecular weight of the synthesized maltitol was 379.08 daltons, corresponding exactly to that of standard maltitol. The relative sweetness of synthesized and standard maltitol was ~90% of that of sucrose. Spot assay on the agar plate showed that maltitol inhibited the growth of Streptococcus mutans DMST 18777 cells. In addition, the MIC and MBC values of synthesized and standard maltitol against S. mutans were also determined as 20 and 40 mg/mL, respectively. These results show that the synthesized maltitol can be produced at high yields and has the potential to be used as an anticariogenic agent in products such as toothpaste.

show abstract

“…13 Additionally, it was highlighted that derivatization of the acceptor at C-1 did not exhibit significant differences in activity whereas changing the configuration of the C-2 and C-4 hydroxyl groups resulted in serious loss of the CGTase efficiency. 14 Nakamura et al showed also by analogy with α-amylase that a pNP group on the anomeric position of the acceptor is not detrimental to the catalysis. 15 Finally, transglycosylation on dodecyl maltoside was recently performed and allowed the access to alkyl oligoglucosides with non-ionic surfactant properties.…”

Section: Introductionmentioning

confidence: 99%

Environmentally benign glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp.

et al. 2014

View full text Add to dashboard Cite

International audienceAn extensive study on the specificity of transglycosylation and disproportionation of Thermoanaerobacterium sp. cyclodextrin glucosyltranferases against aryl glucopyranosides or furanosides was achieved. While a mixture of maltoside and isomaltoside was obtained respectively using p-nitrophenyl glucopyranoside as acceptor, only one regioisomer, namely the p-nitrophenyl α-D-Glcp-(1,3)-α-L-Araf was isolated using p-nitrophenyl arabinofuranoside as acceptor. Interestingly, similar outcomes were found when using p-nitrophenyl galactofuranoside. Furthermore, activation by microwave irradiation resulted in faster reaction times and higher yields and led to glucosidic oligosaccharides with up to 70% conversion. The influence of the anomeric and C-4 configurations of the glycosidic acceptors on the transglycosylation, previously stated for the CGTase family, was not observed and unconventional substrate specificity towards alkyl furanosides was highlighted

show abstract

Synthesis of cellobiose-containing oligosaccharides by intermolecular transglucosylation of cyclodextrin glycosyltransferase from Paenibacillus sp. A11

Cited by 11 publications

References 24 publications

Enhanced 2-O-α-d-Glucopyranosyl-l-ascorbic Acid Synthesis through Iterative Saturation Mutagenesis of Acceptor Subsite Residues in Bacillus stearothermophilus NO2 Cyclodextrin Glycosyltransferase

Enhanced 2-O-α-d-Glucopyranosyl-l-ascorbic Acid Synthesis through Iterative Saturation Mutagenesis of Acceptor Subsite Residues in Bacillus stearothermophilus NO2 Cyclodextrin Glycosyltransferase

Enzymatic Synthesis of Maltitol and Its Inhibitory Effect on the Growth of Streptococcus mutans DMST 18777

Environmentally benign glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp.

Contact Info

Product

Resources

About