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.
Highlights
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/t Bu method, with bromoacetic acid and subsequent nucleophilic replacement of the bromide by reacting with S-4-methoxytrityl- (Mmt)/S-trityl- (Trt) protected aminothiols
Besides the general method for the preparation of the hybrid C, we provide selected examples for the applicability of our method in the synthesis of the protected or deprotected thiol-containing peptide–peptoid hybrids, and the preparation of inter-disulfide bridged peptide–peptoid structures based on the oxidation of different thiol groups of peptoid submonomers that are present on the peptide chain
The derived S-Mmt/Trt-protected aminothiols were applied in the synthesis of thiol-containing peptide–peptoid hybrids (Figure 1)
Summary
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/t Bu 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. Peptides as compounds pharmacokinetics as slow (another drug proteolytic against heavy metal among poisoning, diseases, or cystenuria), uptake into approved cells and rapid cleavage, otherliver factors. N-alkylation of peptides (used to treat paracetamol (acetaminophen) overdose and to loosenpeptides thick mucus canN-acetylcysteine overcome these limitations, structures such as N-alkylated/methylated [1,2]inand individuals with cystic fibrosis or chronic obstructive pulmonary disease), and amifostine
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