347191-35-9

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 442682-26-0 (S)-2-Pyrrolidin-2-yl-thiazole-4-carboxylic acid methyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-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 
• 69610-41-9 Boc-L-Pro-H 

Downstream Products

• 442682-28-2 2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid 
• 347191-37-1 Boc-L-aThr-L-Phe-L-Pro-Thz-OMe 
• 347191-29-1 Boc-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-OMe 
• 347191-27-9 cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-) 
• 347191-28-0 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 
• 358624-95-0 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 494765-98-9 2-((S)-1-{(S)-2-[(2S,3S)-2-((2R,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid methyl ester 
• 494765-91-2 C₄₁H₅₁N₇O₇S 
• 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 
• 404909-88-2 2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid 

Relevant academic research and scientific papers

Synthetic studies on ceratospongamides, cyclic heptapeptides containing thiazole and oxazoline units: Total synthesis of cis, cis-ceratospongamide

A total synthesis of cis, cis-ceratospongamide 1a, a cycloheptapeptide isolated from the Indonesian red alga Ceratodictyon spongiosum and the symbiotic sponge Sigmadocia symbiotica, was accomplished. The heptapeptide chain 8 was produced by a stepwise connection of the following segments: (L-Phe-L-Pro)-thiazole residue, L-Phe-L-Pro-OMe, and L-Ile-L-aThr-OMe. Macrolactamization of 8, followed by cyclization to an oxazoline ring, provided cis, cis-ceratospongamide 1a along with its diastereomer 1c, which was different from the reported trans, trans-ceratospongamide 1b. The structural determination of 1c and its conversion to 1a were successfully achieved.

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.