Investigating Triorthogonal Chemoselectivity. Effect of Azide Substitution on the Triazine Core

Anamika Sharma; Rotimi Sheyi; Ashish Kumar; Ayman El-Faham; Beatriz G de la Torre; Fernando Albericio

doi:10.1021/acs.orglett.9b02878

Investigating Triorthogonal Chemoselectivity. Effect of Azide Substitution on the Triazine Core

Org Lett. 2019 Oct 4;21(19):7888-7892. doi: 10.1021/acs.orglett.9b02878. Epub 2019 Sep 18.

Authors

Anamika Sharma^{1

2}, Rotimi Sheyi¹, Ashish Kumar¹, Ayman El-Faham^{3

4}, Beatriz G de la Torre², Fernando Albericio^{1

3

5}

Affiliations

¹ Peptide Science Laboratory, School of Chemistry and Physics , University of KwaZulu-Natal , Durban 4001 , South Africa.
² KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences , University of KwaZulu-Natal , Durban 4041 , South Africa.
³ Department of Chemistry, College of Science , King Saud University , P.O. Box 2455, Riyadh 11451 , Saudi Arabia.
⁴ Department of Chemistry, Faculty of Science , Alexandria University , P.O. Box 426, Alexandria 21321 , Egypt.
⁵ CIBER-BBN (Networking Centre on Bioengineering, Biomaterials and Nanomedicine) and Department of Organic Chemistry . University of Barcelona , 08028 Barcelona , Spain.

PMID: 31532213
DOI: 10.1021/acs.orglett.9b02878

Abstract

An example of triorthogonal chemoselectivity is reported here for the first time. In this regard, a series of 43 reactions were performed using tridentate s-triazine as a model. In all of the possible cases, the three substitutions were carried out using different nucleophiles at a temperature compatible with biological systems.

Publication types

Research Support, Non-U.S. Gov't