Advanced search
1 file | 1.78 MB Add to list

Trehalose analogues: latest insights in properties and biocatalytic production

Maarten Walmagh (UGent) , Renfei Zhao (UGent) and Tom Desmet (UGent)
Author
Organization
Abstract
Trehalose (alpha-d-glucopyranosyl alpha-d-glucopyranoside) is a non-reducing sugar with unique stabilizing properties due to its symmetrical, low energy structure consisting of two 1,1-anomerically bound glucose moieties. Many applications of this beneficial sugar have been reported in the novel food (nutricals), medical, pharmaceutical and cosmetic industries. Trehalose analogues, like lactotrehalose (alpha-d-glucopyranosyl alpha-d-galactopyranoside) or galactotrehalose (alpha-d-galactopyranosyl alpha-d-galactopyranoside), offer similar benefits as trehalose, but show additional features such as prebiotic or low-calorie sweetener due to their resistance against hydrolysis during digestion. Unfortunately, large-scale chemical production processes for trehalose analogues are not readily available at the moment due to the lack of efficient synthesis methods. Most of the procedures reported in literature suffer from low yields, elevated costs and are far from environmentally friendly. "Greener" alternatives found in the biocatalysis field, including galactosidases, trehalose phosphorylases and TreT-type trehalose synthases are suggested as primary candidates for trehalose analogue production instead. Significant progress has been made in the last decade to turn these into highly efficient biocatalysts and to broaden the variety of useful donor and acceptor sugars. In this review, we aim to provide an overview of the latest insights and future perspectives in trehalose analogue chemistry, applications and production pathways with emphasis on biocatalysis.
Keywords
SCHIZOPHYLLUM-COMMUNE, ENZYMATIC-SYNTHESIS, SYNTHESIZING GLYCOSYLTRANSFERASE, DISACCHARIDE PHOSPHORYLASES, MYCOBACTERIUM-TUBERCULOSIS, PYROCOCCUS-HORIKOSHII, ACCEPTOR SPECIFICITY, ESCHERICHIA-COLI, GRIFOLA-FRONDOSA, EUGLENA-GRACILIS

Downloads

  • Walmagh15 trehalose analogue.pdf
    • full text
    • |
    • open access
    • |
    • PDF
    • |
    • 1.78 MB

Citation

Please use this url to cite or link to this publication:

MLA
Walmagh, Maarten, Renfei Zhao, and Tom Desmet. “Trehalose Analogues: Latest Insights in Properties and Biocatalytic Production.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 16.6 (2015): 13729–13745. Print.
APA
Walmagh, M., Zhao, R., & Desmet, T. (2015). Trehalose analogues: latest insights in properties and biocatalytic production. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 16(6), 13729–13745.
Chicago author-date
Walmagh, Maarten, Renfei Zhao, and Tom Desmet. 2015. “Trehalose Analogues: Latest Insights in Properties and Biocatalytic Production.” International Journal of Molecular Sciences 16 (6): 13729–13745.
Chicago author-date (all authors)
Walmagh, Maarten, Renfei Zhao, and Tom Desmet. 2015. “Trehalose Analogues: Latest Insights in Properties and Biocatalytic Production.” International Journal of Molecular Sciences 16 (6): 13729–13745.
Vancouver
1.
Walmagh M, Zhao R, Desmet T. Trehalose analogues: latest insights in properties and biocatalytic production. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. 2015;16(6):13729–45.
IEEE
[1]
M. Walmagh, R. Zhao, and T. Desmet, “Trehalose analogues: latest insights in properties and biocatalytic production,” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 16, no. 6, pp. 13729–13745, 2015.
@article{6960115,
  abstract     = {{Trehalose (alpha-d-glucopyranosyl alpha-d-glucopyranoside) is a non-reducing sugar with unique stabilizing properties due to its symmetrical, low energy structure consisting of two 1,1-anomerically bound glucose moieties. Many applications of this beneficial sugar have been reported in the novel food (nutricals), medical, pharmaceutical and cosmetic industries. Trehalose analogues, like lactotrehalose (alpha-d-glucopyranosyl alpha-d-galactopyranoside) or galactotrehalose (alpha-d-galactopyranosyl alpha-d-galactopyranoside), offer similar benefits as trehalose, but show additional features such as prebiotic or low-calorie sweetener due to their resistance against hydrolysis during digestion. Unfortunately, large-scale chemical production processes for trehalose analogues are not readily available at the moment due to the lack of efficient synthesis methods. Most of the procedures reported in literature suffer from low yields, elevated costs and are far from environmentally friendly. "Greener" alternatives found in the biocatalysis field, including galactosidases, trehalose phosphorylases and TreT-type trehalose synthases are suggested as primary candidates for trehalose analogue production instead. Significant progress has been made in the last decade to turn these into highly efficient biocatalysts and to broaden the variety of useful donor and acceptor sugars. In this review, we aim to provide an overview of the latest insights and future perspectives in trehalose analogue chemistry, applications and production pathways with emphasis on biocatalysis.}},
  author       = {{Walmagh, Maarten and Zhao, Renfei and Desmet, Tom}},
  issn         = {{1422-0067}},
  journal      = {{INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}},
  keywords     = {{SCHIZOPHYLLUM-COMMUNE,ENZYMATIC-SYNTHESIS,SYNTHESIZING GLYCOSYLTRANSFERASE,DISACCHARIDE PHOSPHORYLASES,MYCOBACTERIUM-TUBERCULOSIS,PYROCOCCUS-HORIKOSHII,ACCEPTOR SPECIFICITY,ESCHERICHIA-COLI,GRIFOLA-FRONDOSA,EUGLENA-GRACILIS}},
  language     = {{eng}},
  number       = {{6}},
  pages        = {{13729--13745}},
  title        = {{Trehalose analogues: latest insights in properties and biocatalytic production}},
  url          = {{http://dx.doi.org/10.3390/ijms160613729}},
  volume       = {{16}},
  year         = {{2015}},
}

Altmetric
View in Altmetric
Web of Science
Times cited: