108283-48-3

Upstream product

• 59859-77-7 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester 
• 90048-49-0 tert-butyl (2S)-2-amino-3-hydroxypropanoate 
• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 124-63-0 methanesulfonyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 119768-50-2 tert-butyl 2-(R)-(tert-butoxycarbonylamino)-3-bromopropanoate 
• 71630-31-4 (R)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 459871-14-8 tert-butyl(2S)-[(tert-butoxycarbonyl)amino]-3-phenylmethanesulfonyloxypropionate 
• 127700-62-3 tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxylate 

Downstream Products

• 684270-46-0 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid 

Relevant academic research and scientific papers

Syntheses of (S)-β-pyrazolylalanine and (S)-quisqualic acid from a serine-derived aziridine

The naturally occurring amino acids (S)-β-pyrazolylalanine and (S)- quisqualic acid are synthesised via the nucleophilic ring-openings of an optically active aziridine by pyrazole and 1,2,4-oxadiazolidine-3,5-dione, respectively.

L-Type amino acid transporter 1 activity of 1,2,3-triazolyl analogs of L-histidine and L-tryptophan

A series of 1,2,3-triazole analogs of the amino acids L-histidine and L-tryptophan were modeled, synthesized and tested for L-type amino acid transporter 1 (LAT1; SLC7A5) activity to guide the design of amino acid-drug conjugates (prodrugs). These triazol

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.

Total synthesis of deamido bleomycin A2, the major catabolite of the antitumor agent bleomycin

Metabolic inactivation of the antitumor antibiotic bleomycin is believed to be mediated exclusively via the action of bleomycin hydrolase, a cysteine proteinase that is widely distributed in nature. While the spectrum of antitumor activity exhibited by th