Solid-phase synthesis of peptide-viologen conjugates

Joseph J Reczek; Elisa Rebolini; Adam R Urbach

doi:10.1021/jo100018f

Solid-phase synthesis of peptide-viologen conjugates

J Org Chem. 2010 Mar 19;75(6):2111-4. doi: 10.1021/jo100018f.

Authors

Joseph J Reczek¹, Elisa Rebolini, Adam R Urbach

Affiliation

¹ Department of Chemistry, Trinity University, San Antonio, Texas 78212, USA.

PMID: 20180557
DOI: 10.1021/jo100018f

Abstract

This paper presents a robust method for the conjugation of viologens to peptides using an amide coupling strategy that is compatible with standard Fmoc solid-phase peptide synthesis. Methodology is presented for monitoring the milligram scale process quantitatively by UV spectroscopy. This chemistry enables the synthesis of a broad range of asymmetric viologens in high yield at room temperature and is compatible with a wide range of functional groups, including amine, guanidinyl, thiol, carboxylic acid, phenol, and indole.

Publication types

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

MeSH terms

Molecular Structure
Peptides / chemical synthesis*
Peptides / chemistry
Viologens / chemical synthesis*
Viologens / chemistry

Substances

Peptides
Viologens