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

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

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 69610-41-9 Boc-L-Pro-H 
• 23420-32-8 N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 
• 38017-89-9 t-butyloxycarbonyl-L-phenylalanyl-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 
• 442682-29-3 methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate 
• 442682-28-2 2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid 
• 347191-35-9 methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate 
• 442899-46-9 C₄₁H₄₉N₇O₆S 
• 1025986-63-3 2-[(S)-1-((S)-2-{[(4S,5R)-2-((1S,2S)-1-{[(S)-1-((S)-2-Amino-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 
• 347191-27-9 cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-) 
• 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 

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.

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.

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

Novel stereospecific dehydration of β-hydroxy-α-amino acids using Martin's sulfurane

The stereospecific dehydration of threo-N-acyl-β-hydroxy-α-amino acid derivatives was performed using Martin's sulfurane to give (Z)-α,β-dehydroamino acids, while erythro-N-acyl-β-hydroxy-α-amino acid amides were converted to 4,5-trans-oxazolines using an

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.