Pyrrole Carboxamide Binol Conjugates: Chiral Receptors for Chemical Inversion of L-amino Acids to D- amino Acids

Authors

  • K. Velmurugan Fluorensic Materials Laboratory, Department of Applied Chemistry, Karunya Institute of Technology and Sciences (Deemed to be University), Karunya Nagar, Coimbatore-641 114, India.
  • Lijun Tang College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University, Jinzhou 121013, P. R. China.
  • J. Prabhu Fluorensic Materials Laboratory, Department of Applied Chemistry, Karunya Institute of Technology and Sciences (Deemed to be University), Karunya Nagar, Coimbatore-641 114, India.
  • R. Nandhakumar Fluorensic Materials Laboratory, Department of Applied Chemistry, Karunya Institute of Technology and Sciences (Deemed to be University), Karunya Nagar, Coimbatore-641 114, India.

DOI:

https://doi.org/10.9734/bpi/pcsr/v5/7899F

Keywords:

Pyrrole carboxamide binol conjugates, chiral recognition, amino acids, chiral inversion, 1H-NMR

Abstract

The chemical inversion of L-amino acids to D-amino acids has been studied using four pyrrole carboxamide binol conjugates 1–4 as Chirality Conversion Reagent’s (CCR’s). This method involves the formation of a Schiff base type imine with a resonance-assisted hydrogen bond (RAHB), which increases the acidity of the proton. The additional hydrogen bonds between the amino acids and the heterocylic moiety of the pendant groups further stabilize the molecule. The conversion efficiency of all the pyrrole carboxamine based receptors 1–4 was found to be comparable with those of the receptors reported earlier.

Published

2022-10-21

How to Cite

K. Velmurugan, Lijun Tang, J. Prabhu, & R. Nandhakumar. (2022). Pyrrole Carboxamide Binol Conjugates: Chiral Receptors for Chemical Inversion of L-amino Acids to D- amino Acids. Progress in Chemical Science Research Vol. 5, 44–56. https://doi.org/10.9734/bpi/pcsr/v5/7899F

Issue

Progress in Chemical Science Research Vol. 5

Section

Chapters