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

• 117175-41-4 tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate 
• 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 
• 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 
• 212009-06-8 ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate 

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

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 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.