KOPS - The Institutional Repository of the University of Konstanz

1‐Picolinyl‐5‐azido Thiosialosides : Versatile Donors for the Stereoselective Construction of Sialyl Linkages

1‐Picolinyl‐5‐azido Thiosialosides : Versatile Donors for the Stereoselective Construction of Sialyl Linkages

Cite This

Files in this item

Files Size Format View

There are no files associated with this item.

CHEN, Jian, Thomas HANSEN, Qing-Ju ZHANG, De-Yong LIU, Yao SUN, Hao YAN, Jeroen D. C. CODÉE, Richard R. SCHMIDT, Jian-Song SUN, 2019. 1‐Picolinyl‐5‐azido Thiosialosides : Versatile Donors for the Stereoselective Construction of Sialyl Linkages. In: Angewandte Chemie International Edition. 58(47), pp. 17000-17008. ISSN 0570-0833. eISSN 1521-3773. Available under: doi: 10.1002/anie.201909177

@article{Chen2019-11-181Pico-47387, title={1‐Picolinyl‐5‐azido Thiosialosides : Versatile Donors for the Stereoselective Construction of Sialyl Linkages}, year={2019}, doi={10.1002/anie.201909177}, number={47}, volume={58}, issn={0570-0833}, journal={Angewandte Chemie International Edition}, pages={17000--17008}, author={Chen, Jian and Hansen, Thomas and Zhang, Qing-Ju and Liu, De-Yong and Sun, Yao and Yan, Hao and Codée, Jeroen D. C. and Schmidt, Richard R. and Sun, Jian-Song} }

Sun, Yao 2019-11-07T13:32:06Z Sun, Jian-Song Hansen, Thomas Liu, De-Yong Hansen, Thomas Zhang, Qing-Ju Schmidt, Richard R. Sun, Jian-Song 1‐Picolinyl‐5‐azido Thiosialosides : Versatile Donors for the Stereoselective Construction of Sialyl Linkages 2019-11-07T13:32:06Z Chen, Jian eng Zhang, Qing-Ju Yan, Hao Chen, Jian With the picolinyl (Pic) group as a C‐1 located directing group and N<sub>3</sub> as versatile precursor for C5‐NH<sub>2</sub>, a novel 1‐Pic‐5‐N<sub>3</sub> thiosialyl donor was designed and synthesized, based on which a new sialylation protocol was established. In comparison to conventional sialylation methods, the new protocol exhibited obvious advantages, including excellent α‐stereoselectivity in the absence of a solvent effect, broad substrate scope encompassing the challenging sialyl 8‐ and 9‐hydroxy groups of sialic acid acceptors, flexibility in sialoside derivative synthesis, high temperature tolerance and easy scalability. In particular, the applicability to the synthesis of complex and bioactive N‐glycan antennae when combined with the MPEP glycosylation protocol via the “latent‐active” strategy has been shown. Mechanistically, the excellent α‐stereoselectivity of the novel sialylation protocol could be attributed to the dramatic electron‐withdrawing effect of the protonated Pic groups, which was supported by control reactions and DFT calculations. 2019-11-18 Yan, Hao Codée, Jeroen D. C. Codée, Jeroen D. C. Sun, Yao Liu, De-Yong Schmidt, Richard R.

This item appears in the following Collection(s)

Search KOPS


Browse

My Account