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

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.

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 Creators:
Seeberger, Peter H.1, Author              
Tuck, Owen T.1, Author
Sletten, Eric T.1, Author              
Danglad-Flores, José Angél1, Author              
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1Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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Free keywords: carbohydrates; glycosylation; thermal stability; activation temperature; glycans
 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.

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Language(s): eng - English
 Dates: 2022-01-152022
 Publication Status: Published in print
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Title: Angewandte Chemie, International Edition in English
  Abbreviation : Angew. Chem., Int. Ed. Engl.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 61 (15) Sequence Number: e202115433 Start / End Page: - Identifier: ISSN: 0570-0833

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Title: Angewandte Chemie
  Abbreviation : Angew. Chem.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 134 (15) Sequence Number: e202115433 Start / End Page: - Identifier: ISSN: 0044-8249