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Jiang J, Kuo CL, Wu L, et al. Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS Cent Sci. 2016;2(5):351-8doi: 10.1021/acscentsci.6b00057.
Jiang, J., Kuo, C. L., Wu, L., Franke, C., Kallemeijn, W. W., Florea, B. I., van Meel, E., van der Marel, G. A., Codée, J. D., Boot, R. G., Davies, G. J., Overkleeft, H. S., & Aerts, J. M. (2016). Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS central science, 2(5), 351-8. https://doi.org/10.1021/acscentsci.6b00057
Jiang, Jianbing, et al. "Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes." ACS central science vol. 2,5 (2016): 351-8. doi: https://doi.org/10.1021/acscentsci.6b00057
Jiang J, Kuo CL, Wu L, Franke C, Kallemeijn WW, Florea BI, van Meel E, van der Marel GA, Codée JD, Boot RG, Davies GJ, Overkleeft HS, Aerts JM. Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes. ACS Cent Sci. 2016 May 25;2(5):351-8. doi: 10.1021/acscentsci.6b00057. Epub 2016 Apr 26. PMID: 27280170; PMCID: PMC4882745.
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ACS Cent Sci. 2016 May 25;2(5):351-8. doi: 10.1021/acscentsci.6b00057. Epub 2016 Apr 26.

Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes.

ACS central science

Jianbing Jiang, Chi-Lin Kuo, Liang Wu, Christian Franke, Wouter W Kallemeijn, Bogdan I Florea, Eline van Meel, Gijsbert A van der Marel, Jeroen D C Codée, Rolf G Boot, Gideon J Davies, Herman S Overkleeft, Johannes M F G Aerts

Affiliations

  1. Department of Bio-organic Synthesis, Leiden Institute of Chemistry, Leiden University , Einsteinweg 55, 2333 CC Leiden, The Netherlands.
  2. Department of Medical Biochemistry, Leiden Institute of Chemistry, Leiden University , Einsteinweg 55, 2333 CC Leiden, The Netherlands.
  3. Department of Chemistry, University of York , Heslington, York, YO10 5DD, U.K.

PMID: 27280170 PMCID: PMC4882745 DOI: 10.1021/acscentsci.6b00057

Abstract

The development of small molecule activity-based probes (ABPs) is an evolving and powerful area of chemistry. There is a major need for synthetically accessible and specific ABPs to advance our understanding of enzymes in health and disease. α-Glucosidases are involved in diverse physiological processes including carbohydrate assimilation in the gastrointestinal tract, glycoprotein processing in the endoplasmic reticulum (ER), and intralysosomal glycogen catabolism. Inherited deficiency of the lysosomal acid α-glucosidase (GAA) causes the lysosomal glycogen storage disorder, Pompe disease. Here, we design a synthetic route for fluorescent and biotin-modified ABPs for in vitro and in situ monitoring of α-glucosidases. We show, through mass spectrometry, gel electrophoresis, and X-ray crystallography, that α-glucopyranose configured cyclophellitol aziridines label distinct retaining α-glucosidases including GAA and ER α-glucosidase II, and that this labeling can be tuned by pH. We illustrate a direct diagnostic application in Pompe disease patient cells, and discuss how the probes may be further exploited for diverse applications.

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