A new, efficient and highly-regioselective approach to synthesis of 6-O-propionyl-d-glucose by using whole-cell biocatalysts

Feng, Guang-li, Wu, Hui, Li, Xiao-feng, Lai, Fu-rao, Zhao, Guang-lei, Yang, Mei-yan and Liu, Hong-wei (2015) A new, efficient and highly-regioselective approach to synthesis of 6-O-propionyl-d-glucose by using whole-cell biocatalysts. Biochemical Engineering Journal, 95 56-61. doi:10.1016/j.bej.2014.12.008


Author Feng, Guang-li
Wu, Hui
Li, Xiao-feng
Lai, Fu-rao
Zhao, Guang-lei
Yang, Mei-yan
Liu, Hong-wei
Title A new, efficient and highly-regioselective approach to synthesis of 6-O-propionyl-d-glucose by using whole-cell biocatalysts
Journal name Biochemical Engineering Journal   Check publisher's open access policy
ISSN 1873-295X
1369-703X
Publication date 2015-03-05
Year available 2014
Sub-type Article (original research)
DOI 10.1016/j.bej.2014.12.008
Open Access Status
Volume 95
Start page 56
End page 61
Total pages 6
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Collection year 2015
Language eng
Formatted abstract
For the first time, whole microbial-cell biocatalysis method was successfully applied by us to the production of glucose esters by transesterification of glucose with vinyl propionate. Among ten bacterial and fungal strains tested, lyophilized cells of Pseudomonasstutzeri strain GIM 1.273 efficiently catalyzed the reaction with the highest conversion and initial rate. 13C NMR analysis showed that the reaction catalyzed by P. stutzeri yielded 6-O regiomer predominantly (>99%), clearly indicating high regioselectivity of the biocatalyst toward the 6-O-hydroxy group of glucose. Efficiency of the reaction catalyzed by lyophilized cells was evidently solvent-dependent. With the exception of acetonitrile-pyridine and tetrahydrofuran-pyridine systems, the substrate conversion rate clearly increased with increasing hydrophobicity of the organic solvent media used. The best results were obtained in isooctane–pyridine (3:7 v/v) system. Other optimal conditions were: water content 2% (v/v), molar ratio of the acyl donor to glucose 10:1, biocatalyst dosage 80 mg/mL and reaction temperature 35 °C, under which glucose conversion and reaction rate were 97.2% and 29.7 mmol/L h over the duration of 24 h. A tenfold scale-up production of the 6-O-glucose ester further demonstrated that whole-cell P.stutzeri was an efficient and highly-regioselective alternative to purified enzymes for synthesis of glucose esters.
Keyword Whole cell
Glucose
Biocatalysis
Transesterification
Optimisation
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Published online ahead of print 18 Dec 2014

Document type: Journal Article
Sub-type: Article (original research)
Collections: School of Agriculture and Food Sciences
Official 2015 Collection
 
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