132402-80-3

Upstream product

• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 1607794-56-8 (S)-N-(allyloxycarbonyl)phenylalanine thioamide 
• 1607794-57-9 (S)-ethyl 2-(1-(allyloxycarbonylamino)-2-phenylethyl)thiazole-4-carboxylate 
• 5241-58-7 L-Phenylalanine amide 
• 70-23-5 ethyl Bromopyruvate 
• 132402-65-4 2-<(S)-1-allyloxycarbonylamino-2-phenyl-ethyl>-4-methoxycarbonyl-(R)-Δ2-thiazoline 
• 132402-58-5 2-allyloxycarbonylamino-3-phenyl-(S)-propioimino ethyl ether 
• 128369-71-1 (S)-methyl-(N-allyloxycarbonyl)phenylalaninate 
• 90508-20-6 N-allyloxycarbonyl-(S)-phenylalanate 
• 132402-73-4 2-<(S)-1-allyloxycarbonylamino-2-phenyl-ethyl>-4-methoxycarbonylthiazole 

Downstream Products

• 132402-83-6 (S)-1-((S)-2-{[2-((S)-1-Allyloxycarbonylamino-2-phenyl-ethyl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

DOLASTATIN 10 ANALOG

Provided herein is a dolastatin 10 analog, useful for preparing conjugates thereof with targeting, diagnostic, imaging and other moieties. Also provided are the conjugates and uses thereof.

Dissecting the structure of thiopeptides: Assessment of thiazoline and tail moieties of baringolin and antibacterial activity optimization

Several analogues of baringolin (1) were prepared to evaluate the role of its characteristic thiazoline ring and pentapeptidic tail with the aim of defining structure-activity relationships for these moieties. The thiazoline ring appeared as a crucial moiety to maintain a broad scope of activities against different Gram-positive bacteria. Further modifications were performed to simplify the structure of the natural product and assess the role of its tail, resulting in an enhanced in vitro performance. Analogue 25, with the thiazole-containing macrocycle and a 4-aminocyclohexane-1-carboxylic acid moiety in place of the pentapeptidic tail, was identified as a much more potent analogue, capable of overcoming the absence of the thiazoline ring and performing extraordinarily well against all strains tested. This is the first library of thiopeptide analogues produced by chemical synthesis alone, which demonstrates the robustness and convenience of the synthetic strategy used.

Synthetic studies towards cyclic peptides. Concise synthesis of thiazoline and thiazole containing amino acids

Concise and efficient syntheses of optically pure thiazoline and thiazole containing amino acids of the constitution (26) and (27), based on simple condensation reactions between cysteine esters and N-protected imino ethers (22) and (25) derived from chir