Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

Sybrin P Schroder; Jasper W van de Sande; Wouter W. Kallemeijn; Chi-Lin Kuo; Marta Artola; Eva J. van Rooden; Jianbing Jiang; Thomas JM Beenakker; Bobby I Florea; Wendy A Offen; Gideon Davies; Adriaan J. Minnaard; Hans Aerts; Jeroen D Codee; Gijsbert A. Van Der Marel; Herman S. Overkleeft

doi:10.1039/C7CC07730K

Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

Sybrin P Schroder, Jasper W van de Sande, Wouter W. Kallemeijn, Chi-Lin Kuo, Marta Artola, Eva J. van Rooden, Jianbing Jiang, Thomas JM Beenakker, Bobby I Florea, Wendy A Offen, Gideon Davies, Adriaan J. Minnaard, Hans Aerts, Jeroen D Codee, Gijsbert A. Van Der Marel, Herman S. Overkleeft

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of [small beta]-glucosidases and [small beta]-galactosidases.

Original language	English
Pages (from-to)	1-5
Number of pages	5
Journal	Chemical Communications
Early online date	6 Nov 2017
DOIs	https://doi.org/10.1039/C7CC07730K
Publication status	E-pub ahead of print - 6 Nov 2017

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10.1039/C7CC07730KLicence: CC BY

c7cc07730k
© 2017, The Author(s).
Accepted author manuscript, 744 KBLicence: CC BY

Glycosylation: Programmes for Observation, Inhibition & Structure-based Exploitation of key carbohydrate-active enzymes
Davies, G. J.
EUROPEAN COMMISSION
1/05/13 → 30/04/19
Project: Research project (funded) › Research

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Schroder, S. P., van de Sande, J. W., Kallemeijn, W. W., Kuo, C-L., Artola, M., van Rooden, E. J., Jiang, J., Beenakker, T. JM., Florea, B. I., Offen, W. A., Davies, G., Minnaard, A. J., Aerts, H., Codee, J. D., Van Der Marel, G. A., & Overkleeft, H. S. (2017). Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines. Chemical Communications, 1-5. https://doi.org/10.1039/C7CC07730K

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title = "Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines",

abstract = "Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of [small beta]-glucosidases and [small beta]-galactosidases.",

author = "Schroder, {Sybrin P} and {van de Sande}, {Jasper W} and Kallemeijn, {Wouter W.} and Chi-Lin Kuo and Marta Artola and {van Rooden}, {Eva J.} and Jianbing Jiang and Beenakker, {Thomas JM} and Florea, {Bobby I} and Offen, {Wendy A} and Gideon Davies and Minnaard, {Adriaan J.} and Hans Aerts and Codee, {Jeroen D} and {Van Der Marel}, {Gijsbert A.} and Overkleeft, {Herman S.}",

note = "{\textcopyright} 2017, The Author(s). ",

year = "2017",

month = nov,

day = "6",

doi = "10.1039/C7CC07730K",

language = "English",

pages = "1--5",

journal = "Chemical communications",

issn = "1359-7345",

publisher = "The Royal Society of Chemistry",

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Schroder, SP, van de Sande, JW, Kallemeijn, WW, Kuo, C-L, Artola, M, van Rooden, EJ, Jiang, J, Beenakker, TJM, Florea, BI, Offen, WA , Davies, G, Minnaard, AJ, Aerts, H, Codee, JD, Van Der Marel, GA & Overkleeft, HS 2017, 'Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines', Chemical Communications, pp. 1-5. https://doi.org/10.1039/C7CC07730K

TY - JOUR

T1 - Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

AU - Schroder, Sybrin P

AU - van de Sande, Jasper W

AU - Kallemeijn, Wouter W.

AU - Kuo, Chi-Lin

AU - Artola, Marta

AU - van Rooden, Eva J.

AU - Jiang, Jianbing

AU - Beenakker, Thomas JM

AU - Florea, Bobby I

AU - Offen, Wendy A

AU - Davies, Gideon

AU - Minnaard, Adriaan J.

AU - Aerts, Hans

AU - Codee, Jeroen D

AU - Van Der Marel, Gijsbert A.

AU - Overkleeft, Herman S.

PY - 2017/11/6

Y1 - 2017/11/6

N2 - Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of [small beta]-glucosidases and [small beta]-galactosidases.

AB - Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of [small beta]-glucosidases and [small beta]-galactosidases.

U2 - 10.1039/C7CC07730K

DO - 10.1039/C7CC07730K

M3 - Article

SP - 1

EP - 5

JO - Chemical communications

JF - Chemical communications

SN - 1359-7345

ER -

Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines

Abstract

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Projects

Glycosylation: Programmes for Observation, Inhibition & Structure-based Exploitation of key carbohydrate-active enzymes

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