Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Abstract

This account describes our efforts dedicated to: 1) the design of glycomimetics aimed at targeting therapeutically relevant carbohydrate processing enzymes, and 2) the observation, characterization, and exploitation of glycosyl cations as a tool for studying the glycosylation reaction. These findings have brought important data regarding this key ionic species as well as innovative strategies to access iminosugars of interest.

1 Introduction

2 The Glycosyl Cation, A Central Species in Glycosciences

2.1 A Selection of the Strategies Developed so far to Gain Insights into Glycosyl Cations Structure

2.2 When Superacids Meet Carbohydrates

3 Chemical Probes to Gain Insights into the Pseudorotational Itinerary of Glycosides During Glycosidic Bond Hydrolysis

3.1 Conformationally Locked Glycosides

3.1.1 The Xylopyranose Case

3.1.2 The Mannopyranose Case

3.2 Conformationally Flexible Iminosugars

3.2.1 Nojirimycin Ring Homologues

3.2.2 Noeuromycin Ring Homologues

3.2.3 Seven-Membered Iminosugar C-Glycosides

4 N-Acetyl-d-glucosamine Mimics

5 Ring Contraction: A Useful Tool to Increase Iminosugar’s Structural Diversity

6 Regioselective Deprotection of Iminosugar C-Glycosides to Introduce Diversity at C2 Position

7 Conclusion

Key words

carbohydrates - glycosyl cation - iminosugars - glycosidases - conformation - superacids

Publication History

Received: 02 October 2020

Accepted: 30 October 2020

Article published online:
03 December 2020

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For another example of 2-acetamidohomoiminosugar, see:
• 132c Hsu C.-H, Schelwies M, Enck S, Huang L.-Y, Huang S.-H, Chang Y.-F, Cheng T.-JR, Cheng W.-C, Wong C.-H. J. Org. Chem. 2014; 79: 8629
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• 133b Kite GC, Fellows LE, Fleet GW. J, Liu PS, Scofield AM, Smith NG. Tetrahedron Lett. 1988; 29: 6483

For β-HNJ, see:
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• 134c Martin OR, Saavedra OM. Tetrahedron Lett. 1995; 36: 799
• 135 Dhavale DD, Matin MM. ARKIVOC 2005; (iii): 110
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• 137 Jagadeesh Y, Tran AT, Luo B, Auberger N, Désiré J, Nakagawa S, Kato A, Zhang Y, Sollogoub M, Blériot Y. Org. Biomol. Chem. 2015; 13: 3446
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• 138b Godin G, Compain P, Martin OR. Org. Lett. 2003; 5: 3269
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• 140 Rychnovsky SD, Bartlett PA. J. Am. Chem. Soc. 1981; 103: 3963
• 141 Cipolla L, La Ferla B, Peri F, Nicotra F. Chem. Commun. 2000; 1289
• 142 Foucart Q, Marrot J, Désiré J, Blériot Y. Org. Lett. 2019; 21: 4821
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