142941-65-9

Upstream product

• 100-39-0 benzyl bromide 
• 80514-76-7 N-triphenylmethyl-(L)-threonine 
• 33640-67-4 (2S,3R)-threonine benzyl ester 
• 76-83-5 trityl chloride 

Downstream Products

• 855259-08-4 Trt-(3-Me-Azy)-Ala-NHMe 
• 867344-50-1 (2S,3S)-3-Methyl-1-trityl-aziridine-2-carboxylic acid ((S)-1-benzylcarbamoyl-2-phenyl-ethyl)-amide 
• 867344-52-3 (2S,3S)-3-Methyl-1-trityl-aziridine-2-carboxylic acid [((S)-1-benzylcarbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-amide 
• 74481-57-5 (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid 
• 86123-06-0 benzyl (2S,3S)-1-H-3-methyl-2-aziridinecarboxylate 
• 86122-64-7 benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-aziridine-2-carboxylate 
• 630107-92-5 Benzyl N-trityl-3(S)-methylaziridine-2(R)-carboxylate 
• 142941-66-0 benzyl (2S,3S)-3-methyl-1-trityl-aziridine-2-carboxylate 

Relevant academic research and scientific papers

Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics

Glycosyl amino acid mimetics of the typical GalNAc-(1→O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics.

Aziridine-2-carboxylic acid-containing peptides: Application to solution- and solid-phase convergent site-selective peptide modification

The development of a method for site- and stereoselective peptide modification using aziridine-2-carboxylic acid-containing peptides is described. A solid-phase peptide synthesis methodology that allows for the rapid generation of peptides incorporating the aziridine residue has been developed. The unique electrophilic nature of this nonproteinogenic amino acid allows for site-selective conjugation with various thiol nucleophiles, such as anomeric carbohydrate thiols, farnesyl thiol, and biochemical tags, both in solution and on solid support. This strategy, combined with native chemical ligation, provides convergent and rapid access to complex thioglycoconjugates.

Conjugation of selenols with aziridine-2-carboxylic acid-containing peptides

The addition of PhSeH to aziridine-2-carboxylic acid containing peptides is described, thus expanding the scope of nucleophiles for the opening of this class of electrophilic peptide substrates. The process offers a new strategy for the generation of usef