Solid-Phase Synthesis of 2-Benzothiazolyl and 2-(Aminophenyl)benzothiazolyl Amino Acids and Peptides

Spyridon Mourtas; Vasileios Athanasopoulos; Dimitrios Gatos; Kleomenis Barlos

doi:10.3390/molecules28145412

Solid-Phase Synthesis of 2-Benzothiazolyl and 2-(Aminophenyl)benzothiazolyl Amino Acids and Peptides

Molecules. 2023 Jul 14;28(14):5412. doi: 10.3390/molecules28145412.

Authors

Spyridon Mourtas¹, Vasileios Athanasopoulos¹, Dimitrios Gatos¹, Kleomenis Barlos²

Affiliations

¹ Department of Chemistry, University of Patras, 26510 Rio Patras, Greece.
² CBL-Patras, Patras Industrial Area, Block 1, 25018 Patras, Greece.

Abstract

2-benzothiazoles and 2-(aminophenyl)benzothiazoles represent biologically interesting heterocycles with high pharmacological activity. The combination of these heterocycles with amino acids and peptides is of special interest, as such structures combine the advantages of amino acids and peptides with the advantages of the 2-benzothiazolyl and 2-(aminophenyl)benzothiazolyl pharmacophore group. In this work, we developed an easy and efficient method for the solid-phase synthesis of 2-benzothiazolyl (BTH) and 2-(aminophenyl)benzothiazolyl (AP-BTH) C-terminal modified amino acids and peptides with high chiral purity.

Keywords: 2-(aminophenyl)benzothiazoles; 2-benzothiazoles; amino acids; chiral purity; racemization; solid-phase synthesis.

MeSH terms

Amines / chemistry
Amino Acids* / chemistry
Benzothiazoles / chemistry
Peptides
Solid-Phase Synthesis Techniques*

Substances

Amino Acids
Amines
Benzothiazoles
Peptides

Grants and funding

81762/University of Patras