A stereoselective protocol for the synthesis of a molecular cinquefoil (51) knot

Jing Han; Zekun Liu; Raorao Yang; Fan Yang; Zhi-Hui Zhang; Liang Zhang

doi:10.1016/j.xpro.2023.102398

A stereoselective protocol for the synthesis of a molecular cinquefoil (5₁) knot

STAR Protoc. 2023 Sep 15;4(3):102398. doi: 10.1016/j.xpro.2023.102398. Epub 2023 Jul 4.

Authors

Jing Han¹, Zekun Liu², Raorao Yang¹, Fan Yang², Zhi-Hui Zhang³, Liang Zhang⁴

Affiliations

¹ School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, P. R. China.
³ School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China. Electronic address: zhangzhihui@chem.ecnu.edu.cn.
⁴ School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, P. R. China. Electronic address: liangzhang@chem.ecnu.edu.cn.

Abstract

Here, we present a protocol for the complete stereoselective synthesis of a molecular 5₁ knot. Enantiopure chiral ligands serve as the starting point, while Zn(OTf)₂ acts as the template, facilitating the quantitative formation of pentameric circular helicates with 100% d.e. A subsequent sequence of ring-closing metathesis and demetalation steps transforms the structure into a fully organic 5₁ knot. This protocol expands the scope of strategies employed for chiral knot preparation and paves the way for more complex molecular topologies. For complete details on the use and execution of this protocol, please refer to Zhang et al.¹.

Keywords: Biotechnology and bioengineering; Chemistry; Protein Biochemistry.

Publication types

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

MeSH terms

Mesylates
Potentilla*
Zinc Compounds*

Substances

zinc trifluoromethanesulfonate
Mesylates
Zinc Compounds