English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Towards a systematic understanding of the influence of temperature on glycosylation reactions

MPS-Authors
/persons/resource/persons121849

Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

Tuck,  Owen T.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons242896

Sletten,  Eric T.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons213288

Danglad-Flores,  José Angél
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

External Resource
No external resources are shared
Fulltext (public)

Article.pdf
(Publisher version), 4MB

Article_de.pdf
(Publisher version), 4MB

Supplementary Material (public)
There is no public supplementary material available
Citation

Seeberger, P. H., Tuck, O. T., Sletten, E. T., & Danglad-Flores, J. A. (2022). Towards a systematic understanding of the influence of temperature on glycosylation reactions. Angewandte Chemie, International Edition in English, 61(15): e202115433. doi:10.1002/anie.202115433.


Cite as: http://hdl.handle.net/21.11116/0000-0009-D243-E
Abstract
Glycosidic bond formation is a continual challenge for practitioners. Aiming to enhance the reproducibility and efficiency of oligosaccharide synthesis, we studied the relationship between glycosyl donor activation and reaction temperature. A novel semi-automated assay revealed diverse responses of members of a panel of thioglycosides to activation at various temperatures. The patterns of protecting groups and the thiol aglycon combine to cause remarkable differences in temperature sensitivity among glycosylating agents. We introduce the concept of donor activation temperature to capture experimental insights, reasoning that glycosylations performed below this reference temperature evade deleterious side reactions. Activation temperatures enable a simplified temperature treatment and facilitate optimization of glycosylating agent (building block) usage. Isothermal glycosylation below the activation temperature halved the equivalents of building block required in comparison to the standard ‘ramp’ regime used in solution- and solid-phase oligosaccharide synthesis to-date.