259794-28-0

Basic information

• Product Name: cis,cis-Ceratospongamide
• Synonyms: cis,cis-Ceratospongamide
• CAS NO: 259794-28-0
• Molecular Weight: 767.949
• Mol File: 259794-28-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: cis,cis-Ceratospongamide(CAS DataBase Reference)
• NIST Chemistry Reference: cis,cis-Ceratospongamide(259794-28-0)
• EPA Substance Registry System: cis,cis-Ceratospongamide(259794-28-0)

Safety Data

• Hazardous Substances Data: 259794-28-0(Hazardous Substances Data)

Upstream product

• 442899-46-9 C₄₁H₄₉N₇O₆S 
• 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 
• 662723-01-5 L-Phe-L-Pro-Thz-OMe 
• 442682-26-0 (S)-2-Pyrrolidin-2-yl-thiazole-4-carboxylic acid methyl ester 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 83825-04-1 L-phenylalanine-L-proline methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 404909-85-9 2-{1-[2-({2-[1-({1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-2-methyl-butyl]-5-methyl-4,5-dihydro-oxazole-4-carbonyl}-amino)-3-phenyl-propionyl]-pyrrolidin-2-yl}-thiazole-4-carboxylic acid ethyl ester 
• 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 
• 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 articles and documents

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.

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.