Synthesis of taurine-containing peptides, sulfonopeptides, and N- and O-conjugates

Peter Vertesaljai; Suvendu Biswas; Iryna Lebedyeva; Evan Broggi; Abdullah M Asiri; Alan R Katritzky

doi:10.1021/jo500181g

Synthesis of taurine-containing peptides, sulfonopeptides, and N- and O-conjugates

J Org Chem. 2014 Mar 21;79(6):2688-93. doi: 10.1021/jo500181g. Epub 2014 Mar 11.

Authors

Peter Vertesaljai¹, Suvendu Biswas, Iryna Lebedyeva, Evan Broggi, Abdullah M Asiri, Alan R Katritzky

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.

PMID: 24568296
DOI: 10.1021/jo500181g

Abstract

Taurine-containing water-soluble peptidomimetics were designed and synthesized. N-terminal taurine acylations allowed synthesis of a number of taurine-containing peptides. N-protection of taurine with Cbz and SO2-activation with benzotriazole followed by coupling with various amino esters, dipeptides and nucleophiles provided taurine N- and O-conjugates and sulfonopeptides.

Publication types

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

MeSH terms

Nitrogen / chemistry*
Oxygen / chemistry*
Peptides / chemical synthesis*
Peptides / chemistry
Peptidomimetics / chemistry*
Sulfhydryl Compounds / chemistry*
Taurine / chemical synthesis*
Taurine / chemistry
Triazoles / chemistry*

Substances

Peptides
Peptidomimetics
Sulfhydryl Compounds
Triazoles
Taurine
benzotriazole
Nitrogen
Oxygen