141672-08-4

Usage

Uses

Used in Pharmaceutical Applications:
(2Z,5R,6S,9S,12S,13S,16R)-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-9-(1-methylethyl)-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid is used as a pharmaceutical agent for its potential therapeutic properties. The presence of multiple functional groups and its complex molecular structure may contribute to its interaction with biological targets, making it a promising candidate for drug development.
Used in Materials Science Applications:
In materials science, (2Z,5R,6S,9S,12S,13S,16R)-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-9-(1-methylethyl)-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid can be used to develop new materials with unique properties. Its functional groups and molecular structure may allow for the creation of novel materials with specific characteristics, such as improved strength, flexibility, or chemical resistance.
Used in Organic Synthesis Applications:
(2Z,5R,6S,9S,12S,13S,16R)-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-9-(1-methylethyl)-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid can be utilized as a building block or intermediate in organic synthesis. Its complex structure and functional groups may enable the synthesis of new organic compounds with various applications, such as pharmaceuticals, agrochemicals, or specialty chemicals.

Upstream product

• 170872-85-2 dimethyl motuporine hydrate 
• 223923-83-9 Dimethylmotuporin 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 134440-89-4 (2R,3S)-3-methoxy-2-methyl-4-phenylbutanal 
• 55227-00-4 α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester 
• 134440-92-9 (2S,3S,4E,6E,8S,9S)-3-(tert-butoxycarbonyl)amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid 
• 110473-10-4 N-Boc-D-Glu α-methyl ester 
• 226067-39-6 C₄₇H₇₃N₅O₁₄ 
• 180133-63-5 (4S,5S,2E)-2-iodo-5-methoxy-4-methyl-6-phenyl-2-hexene 
• 180133-61-3 (4R,5S)-4-methyl-5-methoxy-6-phenyl-2-hexyne 
• 184354-30-1 (3R,4S)-1,1-dibromo-4-methoxy-5-phenyl-3-methyl-pent-1-ene 
• 194149-69-4 (E)-(4S, 5S)-methyl-4-azido-6-hydroxy-5-methyl-hex-2-enoate 
• 194149-74-1 [(1R,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 194149-66-1 (E)-(3R,4S)-1-iodo-3-(N-tert-butoxycarbonyl)amino-5-(tert-butyldimethylsiloxy)-4-methyl-pent-1-ene 

Downstream Products

• 223923-83-9 Dimethylmotuporin 

Relevant academic research and scientific papers

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

A highly convergent asymmetric synthesis of the protein phosphatase inhibitor motuporin 1a is described. Synthesis and coupling of the individual peptide fragments [34 + -35 → 51] followed by macrocyclization afforded the fully protected motuporin precursor 33, which is converted to the natural product by dehydration and ester hydrolysis, Six of the eight stereogenic centers associated with the natural product were introduced using asymmetric crotylsilane bond construction methodology. Our approach features an efficient Pd(0)-catalyzed cross-coupling reaction between a configurationally well-defined vinyl zinc intermediate 22 and an (E)-vinyl iodide 7, which afforded compound 43, resulting in the construction of the trisubstituted (E,E)-diene system of the motuporin side chain. Improved reaction conditions for macrocyclization in the formation of 33 are also detailed.

Total synthesis of motuporin and 5-[L-Ala]-motuporin

Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N- methyldehydrobutyrine residue masked as a threonine, but significant C- terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-1 (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.

Total synthesis of motuporin (nodularin-v)

The serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (mic