Host-Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry

Hadi Gholami; Mercy Anyika; Jun Zhang; Chrysoula Vasileiou; Babak Borhan

doi:10.1002/chem.201601064

Host-Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry

Chemistry. 2016 Jun 27;22(27):9235-9. doi: 10.1002/chem.201601064. Epub 2016 Jun 3.

Authors

Hadi Gholami¹, Mercy Anyika¹, Jun Zhang¹, Chrysoula Vasileiou¹, Babak Borhan²

Affiliations

¹ Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
² Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA. babak@chemistry.msu.edu.

PMID: 27258557
DOI: 10.1002/chem.201601064

Abstract

The absolute stereochemistry of cyanohydrins, derived from ketones and aldehydes, is obtained routinely, in a microscale and derivatization-free manner, upon their complexation with Zn-MAPOL, a zincated porphyrin host with a binding pocket comprised of a biphenol core. The host-guest complex leads to observable exciton-coupled circular dichroism (ECCD), the sign of which is easily correlated to the absolute stereochemistry of the bound cyanohydrin. A working model, based on the ECCD signal of cyanohydrins with known configuration, is proposed.

Keywords: ECCD; MAPOL; circular dichroism; cyanohydrin; stereochemistry.