347191-27-9

Basic information

• Product Name: cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)
• Synonyms: cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)
• CAS NO: 347191-27-9
• Molecular Weight: 785.965
• Mol File: 347191-27-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)(CAS DataBase Reference)
• NIST Chemistry Reference: cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)(347191-27-9)
• EPA Substance Registry System: cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)(347191-27-9)

Safety Data

• Hazardous Substances Data: 347191-27-9(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 83825-04-1 L-phenylalanine-L-proline methyl ester 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 404909-84-8 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 ethyl ester 
• 404909-87-1 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester 
• 404909-83-7 2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester 
• 404909-86-0 2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester 
• 212009-06-8 ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate 
• 117175-41-4 tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate 
• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 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 
• 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 

Downstream Products

• 259794-28-0 cis,cis-Ceratospongamide 

Relevant articles and documents

Kinetic control of proline amide rotamers: Total synthesis of trans,trans- and cis,cis-ceratospongamide

Ceratospongamide is a cyclic peptide natural product that is biosynthesized as a mixture of two proline rotamers. Remarkably, these rotamers do not detectably interconvert at temperatures up to 100 °C. Here we report high-yielding syntheses of each rotame

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.