Sugar-based novel chiral macrocycles for inclusion applications and chiral recognition

Ankita Singh; Vinod Khatri; Shashwat Malhotra; Ashok K Prasad

doi:10.1016/j.carres.2015.12.006

Sugar-based novel chiral macrocycles for inclusion applications and chiral recognition

Carbohydr Res. 2016 Feb 8:421:25-32. doi: 10.1016/j.carres.2015.12.006. Epub 2015 Dec 23.

Authors

Ankita Singh¹, Vinod Khatri¹, Shashwat Malhotra¹, Ashok K Prasad²

Affiliations

¹ Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India.
² Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India. Electronic address: ashokenzyme@gmail.com.

PMID: 26774875
DOI: 10.1016/j.carres.2015.12.006

Abstract

A convergent template assisted synthesis of sugar-based chiral macrocycles has been achieved. The host-guest inclusion studies have revealed significant interactions of the synthesized macrocycle with primary over secondary ammonium salt. The chiral macrocyle also discriminates between D- and L-phenylalanine methyl ester hydrochlorides as revealed by (1)H NMR spectral studies on the mixture of the host and the guest molecules.

Keywords: Benzyl ammonium perchlorate; Chiral recognition; Click reaction; Macrocycle; Phenylalanine; Template assisted.

Publication types

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

MeSH terms

Glucosamine / chemistry*
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry
Molecular Structure
Salts / chemistry

Substances

Macrocyclic Compounds
Salts
Glucosamine