494765-98-9

Upstream product

• 13139-16-7 N-tert-butoxycarbonyl-D-alloisoleucine 
• 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 
• 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 
• 69610-41-9 Boc-L-Pro-H 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 

Downstream Products

• 494765-90-1 2-(1-{2-[2-(2-{[1-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid methyl ester 
• 494765-91-2 C₄₁H₅₁N₇O₇S 

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.