Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides

Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides

<i>N</i>-mercaptoalkylglycine residues were inserted into peptides by reacting <i>N</i>-free amino groups of peptides, which were initially synthesized on 2-chlorotrityl resin (Cltr) using the Fmoc/<sup>t</sup>Bu method, with bromoacetic acid and subsequent nucleo...

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Main Authors: Spyridon Mourtas, Dimitrios Gatos, Kleomenis Barlos
Format: Article
Language:English
Published: MDPI AG 2019-11-01
Series:Molecules
Subjects:
aminothiols
oxidation
peptoids
solid-phase synthesis
2-chlorotrityl resin
Online Access:https://www.mdpi.com/1420-3049/24/23/4261
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spelling doaj-f80b220065fb4f3f8ff28ecff74f30532020-11-25T01:44:04ZengMDPI AGMolecules1420-30492019-11-012423426110.3390/molecules24234261molecules24234261Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into PeptidesSpyridon Mourtas0Dimitrios Gatos1Kleomenis Barlos2Department of Chemistry, University of Patras, 26510 Rio Patras, GreeceDepartment of Chemistry, University of Patras, 26510 Rio Patras, GreeceDepartment of Chemistry, University of Patras, 26510 Rio Patras, Greece<i>N</i>-mercaptoalkylglycine residues were inserted into peptides by reacting <i>N</i>-free amino groups of peptides, which were initially synthesized on 2-chlorotrityl resin (Cltr) using the Fmoc/<sup>t</sup>Bu method, with bromoacetic acid and subsequent nucleophilic replacement of the bromide by reacting with <i>S</i>-4-methoxytrityl- (Mmt)/<i>S</i>-trityl- (Trt) protected aminothiols. The synthesized thiols containing peptide&#8722;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.https://www.mdpi.com/1420-3049/24/23/4261aminothiolsoxidationpeptoidssolid-phase synthesis2-chlorotrityl resin
collection DOAJ
language English
format Article
sources DOAJ
author Spyridon Mourtas
Dimitrios Gatos
Kleomenis Barlos
spellingShingle Spyridon Mourtas
Dimitrios Gatos
Kleomenis Barlos
Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
Molecules
aminothiols
oxidation
peptoids
solid-phase synthesis
2-chlorotrityl resin
author_facet Spyridon Mourtas
Dimitrios Gatos
Kleomenis Barlos
author_sort Spyridon Mourtas
title Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
title_short Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
title_full Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
title_fullStr Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
title_full_unstemmed Solid-Phase Insertion of <i>N</i>-mercaptoalkylglycine Residues into Peptides
title_sort solid-phase insertion of <i>n</i>-mercaptoalkylglycine residues into peptides
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-11-01
description <i>N</i>-mercaptoalkylglycine residues were inserted into peptides by reacting <i>N</i>-free amino groups of peptides, which were initially synthesized on 2-chlorotrityl resin (Cltr) using the Fmoc/<sup>t</sup>Bu method, with bromoacetic acid and subsequent nucleophilic replacement of the bromide by reacting with <i>S</i>-4-methoxytrityl- (Mmt)/<i>S</i>-trityl- (Trt) protected aminothiols. The synthesized thiols containing peptide&#8722;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.
topic aminothiols
oxidation
peptoids
solid-phase synthesis
2-chlorotrityl resin
url https://www.mdpi.com/1420-3049/24/23/4261
work_keys_str_mv AT spyridonmourtas solidphaseinsertionofinimercaptoalkylglycineresiduesintopeptides
AT dimitriosgatos solidphaseinsertionofinimercaptoalkylglycineresiduesintopeptides
AT kleomenisbarlos solidphaseinsertionofinimercaptoalkylglycineresiduesintopeptides
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