Synthesis and conformational analysis of a potentially super-armed glucuronidation donor

Steinacher, Michael; Svatunek, Dennis; Weil, Matthias; Mohammadi, Bagher; Gärtner, Peter

doi:10.1007/s00706-022-03009-4

Record link:

http://hdl.handle.net/20.500.12708/142148

Title:

Synthesis and conformational analysis of a potentially super-armed glucuronidation donor

Citation:

Steinacher, M., Svatunek, D., Weil, M., Mohammadi, B., & Gärtner, P. (2022). Synthesis and conformational analysis of a potentially super-armed glucuronidation donor. Monatshefte Für Chemie - Chemical Monthly. https://doi.org/10.1007/s00706-022-03009-4

Publisher DOI:

10.1007/s00706-022-03009-4

CatalogPlus:

AC17203339

Publication Type:

Article - Original Research Article

Language:

English

Authors:

Steinacher, Michael
Svatunek, Dennis
Weil, Matthias
Mohammadi, Bagher
Gärtner, Peter

Organisational Unit:

E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie

Journal:

Monatshefte für Chemie - Chemical Monthly

ISSN:

0026-9247

Date (published):

10-Dec-2022

Number of Pages:

Publisher:

SPRINGER WIEN

Peer reviewed:

Yes

Keywords:

Carbohydrates; Conformation; Crystal structure; Protecting groups

Abstract:

The concise synthesis of a potentially “super-armed” glucuronidation donor is reported. The α-anomer was crystallized and analyzed by single crystal X-ray diffraction. The pyranose ring was found to be in a twist-boat conformation in the solid state. To confirm the relevance of this finding for the solution state, and explain the failure of analysis by NMR, DFT calculations were performed. They revealed the twist-boat to be the dominant among a group of several possible conformers at ambient temperature.

Research facilities:

Vienna Scientific Cluster

Research Areas:

Beyond TUW-research foci: 100%

Science Branch:

1040 - Chemie: 100%

License:

CC BY 4.0