Solid-Phase Insertion of N-mercaptoalkylglycine Residues into Peptides

Spyridon Mourtas; Dimitrios Gatos; Kleomenis Barlos

doi:10.3390/molecules24234261

Solid-Phase Insertion of N-mercaptoalkylglycine Residues into Peptides

Molecules. 2019 Nov 22;24(23):4261. doi: 10.3390/molecules24234261.

Authors

Spyridon Mourtas^{1

2}, Dimitrios Gatos¹, Kleomenis Barlos^{1

3}

Affiliations

¹ Department of Chemistry, University of Patras, 26510 Rio Patras, Greece.
² Institute of Chemical Engineering Sciences of the Foundation for Research and Technology Hellas (FORTH/IEC-HT), 26504 Rio Patras, Greece.
³ CBL-Patras, Patras Industrial Area, Block 1, 25018 Patras, Greece.

Abstract

N-mercaptoalkylglycine residues were inserted into peptides by reacting N-free amino groups of peptides, which were initially synthesized on 2-chlorotrityl resin (Cltr) using the Fmoc/^tBu method, with bromoacetic acid and subsequent nucleophilic replacement of the bromide by reacting with S-4-methoxytrityl- (Mmt)/S-trityl- (Trt) protected aminothiols. The synthesized thiols containing peptide-peptoid hybrids were cleaved from the resin, either protected by treatment with dichloromethane (DCM)/trifluoroethanol (TFE)/acetic acid (AcOH) (7:2:1), or deprotected (fully or partially) by treatment with trifluoroacetic acid (TFA) solution using triethylsilane (TES) as a scavenger.

Keywords: 2-chlorotrityl resin; aminothiols; oxidation; peptoids; solid-phase synthesis.

MeSH terms

Glycine / chemistry*
Molecular Structure
Peptides / chemistry*
Peptoids / chemistry
Solid-Phase Synthesis Techniques
Sulfhydryl Compounds / chemical synthesis
Sulfhydryl Compounds / chemistry

Substances

Peptides
Peptoids
Sulfhydryl Compounds
Glycine