358624-95-0

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 347191-31-5 (2S)-2-(1-tert-butoxycarbonylpyrrolidin-2-yl)-thiazolidine-4-carboxylic acid methyl ester 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 662723-01-5 L-Phe-L-Pro-Thz-OMe 
• 442682-26-0 (S)-2-Pyrrolidin-2-yl-thiazole-4-carboxylic acid methyl ester 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 347191-29-1 Boc-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-OMe 
• 347191-37-1 Boc-L-aThr-L-Phe-L-Pro-Thz-OMe 
• 347191-35-9 methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate 
• 347191-33-7 Boc-L-Pro-Thz-OMe 
• 38017-89-9 t-butyloxycarbonyl-L-phenylalanyl-L-proline methyl ester 
• 69610-41-9 Boc-L-Pro-H 
• 69936-03-4 (1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate 

Downstream Products

• 347191-27-9 cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-) 
• 259794-28-0 cis,cis-Ceratospongamide 

Relevant academic research and scientific papers

Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin

The first total synthesis of cis,cis-ceratospongamide (cyclo[L-Pro-L-Ile-Me-oxazoline-L-Phe-L-Pro-thiazole-L-Phe-]) was accomplished and confirmed by X-ray crystal analysis. The heating of cis,cis-ceratospongamide in DMSO converted it not to the trans,trans isomer but to the trans,trans-[D-allo-Ile]-ceratospongamide, which was confirmed by total synthesis. Its solution conformation was constructed by the dynamic simulated annealing method using ROE cross peaks, revealing a rounded and flat ring structure which is in contrast with the slim and tight structure of cis,cis isomer. The results shows that the trans,trans-[D-allo-Ile] isomer is the main thermal product of cis,cis-ceratospongamide.

Total synthesis of cis,cis-ceratospongamide, a bioactive thiazole-containing cyclic peptide from marine origin

The first total synthesis of cis,cis-ceratospongamide (1a), isolated from marine source, was accomplished via thiazole synthesis using CMD methodology, DEPC-mediated peptide coupling, macrolactamization, and cyclodehydration. Comparison of the cyclization sites and coupling reagents in the macrolactamization step was also investigated.