ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img
RETURN TO ISSUEPREVBiotechnology and Bi...Biotechnology and Biological TransformationsNEXT

Sweet Biotechnology: Enzymatic Production and Digestibility Screening of Novel Kojibiose and Nigerose Analogues

  • Shari Dhaene
    Shari Dhaene
    Department of Biotechnology, Centre for Synthetic Biology (CSB), Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
    More by Shari Dhaene
  • Amar Van Laar
    Amar Van Laar
    Department of Food technology, Safety and Health, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
  • Marc De Doncker
    Marc De Doncker
    Department of Biotechnology, Centre for Synthetic Biology (CSB), Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
  • Emma De Beul
    Emma De Beul
    Department of Biotechnology, Centre for Synthetic Biology (CSB), Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
    More by Emma De Beul
  • Koen Beerens
    Koen Beerens
    Department of Biotechnology, Centre for Synthetic Biology (CSB), Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
    More by Koen Beerens
  • Charlotte Grootaert
    Charlotte Grootaert
    Department of Food technology, Safety and Health, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
  • Jurgen Caroen
    Jurgen Caroen
    Department of Organic and Macromolecular Chemistry, Laboratory for Organic and Bio-Organic Synthesis (LOBOS), Ghent University, Krijgslaan 281 S4, B-9000 Ghent, Belgium
  • Johan Van der Eycken
    Johan Van der Eycken
    Department of Organic and Macromolecular Chemistry, Laboratory for Organic and Bio-Organic Synthesis (LOBOS), Ghent University, Krijgslaan 281 S4, B-9000 Ghent, Belgium
  • John Van Camp*
    John Van Camp
    Department of Food technology, Safety and Health, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
    *Email: [email protected]
  • , and 
  • Tom Desmet*
    Tom Desmet
    Department of Biotechnology, Centre for Synthetic Biology (CSB), Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
    *Email: [email protected]
    More by Tom Desmet
Cite this: J. Agric. Food Chem. 2022, 70, 11, 3502–3511
Publication Date (Web):March 10, 2022
https://doi.org/10.1021/acs.jafc.1c07709
Copyright © 2022 American Chemical Society
  • Editors Choice

Article Views

5763

Altmetric

-

Citations

LEARN ABOUT THESE METRICS
Read OnlinePDF (1 MB)
Supporting Info (1)»

Abstract

Abstract Image

In view of the global pandemic of obesity and related metabolic diseases, there is an increased interest in alternative carbohydrates with promising physiochemical and health-related properties as a potential replacement for traditional sugars. However, our current knowledge is limited to only a small selection of carbohydrates, whereas the majority of alternative rare carbohydrates and especially their properties remain to be investigated. Unraveling their potential properties, like digestibility and glycemic content, could unlock their use in industrial applications. Here, we describe the enzymatic production and in vitro digestibility of three novel glycosides, namely, two kojibiose analogues (i.e., d-Glcp-α-1,2-d-Gal and d-Glcp-α-1,2-d-Rib) and one nigerose analogue (i.e., d-Glcp-α-1,3-l-Ara). These novel sugars were discovered after an intensive acceptor screening with a sucrose phosphorylase originating from Bifidobacterium adolescentis (BaSP). Optimization and upscaling of this process led to roughly 100 g of these disaccharides. Digestibility, absorption, and caloric potential were assessed using brush border enzymes of rat origin and human intestinal Caco-2 cells. The rare disaccharides showed a reduced digestibility and a limited impact on energy metabolism, which was structure-dependent and even more pronounced for the three novel disaccharides in comparison to their respective glucobioses, translating to a low-caloric potential for these novel rare disaccharides.

Supporting Information

ARTICLE SECTIONS
Jump To

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jafc.1c07709.

  • Structure determination of disaccharides d-Glcp-α-1,2-d-Gal, d-Glcp-α-1,2-d-Rib, and d-Glcp-α-1,3-l-Ara; structure determination of d-Glcp-α-1,2-d-Rib; diagnostic NMR correlations for predominant isomer (α-d-Glcp-1,2-β-d-Ribp) in D2O (400 MHz) (Figure S1); absolute ATP content (μM) and changes in supernatant disaccharide concentrations (μM) during cellular sugar exposures (14 mM, 24 h) (Table S1); HPAEC-PAD standards (Figure S2); preparative liquid chromatography profile of all three novel sugars (d-Glcp-α-1,2-d-Gal, d-Glcp-α-1,2-d-Rib, and d-Glcp-α-1,3-l-Ara) (Figure S3); purity determined via HPAEC-PAD for all three novel sugars (d-Glcp-α1,2-d-Gal, d-Glcp-α1,2-d-Rib, and d-Glcp-α1,3-l-Ara) (Figure S4); 1H NMR and 13C (APT) spectra of compound d-Glcp-α-1,2-d-Gal (Figures S5–S8); 1H NMR, 13C (APT), COSY NMR, HSQC NMR, and HMBS NMR spectra of compound d-Glcp-α-1,2-d-Rib (Figures S9–S15); and 1H NMR and 13C (APT) spectra of compound d-Glcp-α-1,3-l-Ara (Figures S16–S18) (PDF)

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 1 publications.

  1. Stanley O. Onyango, Koen Beerens, Qiqiong Li, John Van Camp, Tom Desmet, Tom Van de Wiele. Glycosidic linkage of rare and new-to-nature disaccharides reshapes gut microbiota in vitro. Food Chemistry 2023, 411 , 135440. https://doi.org/10.1016/j.foodchem.2023.135440

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect