Jasplakinolide

Base Information

• Chemical Name: Jasplakinolide
• CAS No.: 102396-24-7
• Molecular Formula: C₃₆H₄₅BrN₄O₆
• Molecular Weight: 709.68
• NSC Number: 613009
• DSSTox Substance ID: DTXSID30893487
• Wikidata: Q27134619
• Metabolomics Workbench ID: 64396
• ChEMBL ID: CHEMBL257166
• Mol file: 102396-24-7.mol

Synonyms:jaspamide;jasplakinolide;NSC 613009

Chemical Property of Jasplakinolide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 110℃ (decomposition)
• Boiling Point: 968.3°Cat760mmHg
• Flash Point: 539.4°C
• PSA: 140.83000
• Density: 1.227g/cm³
• LogP: 6.13250
• Storage Temp.: ?20°C
• Solubility.: DMSO: >2mg/mL
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 708.25225
• Heavy Atom Count: 47
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

Jasplakinolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(OC(=O)CC(NC(=O)C(N(C(=O)C(NC(=O)C(CC(=C1)C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C
• Isomeric SMILES: C[C@@H]\1C[C@@H](OC(=O)C[C@@H](NC(=O)[C@H](N(C(=O)[C@@H](NC(=O)[C@H](C/C(=C1)/C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C
• Description: Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. JASPLAKINOLIDE is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.
• Uses: Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies. Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. JASPLAKINOLIDE is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development. Jasplakinolide has been used to analyze its influence on sciatic nerve guidance effect in vivo in chicken embryos. It has also been used to apply on the control cells for the treatment for blocking actin dynamics.

Technology Process of Jasplakinolide

There total 100 articles about Jasplakinolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine ρ-lactone (161722-19-6) → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.3987/COM-94-S(B)52

Reference yield: 90.0%

C45H65N4O6SiBr (943858-43-3) → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1021/ol070855h

Reference yield:

C22H29NO5 → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 83 percent / LiBH₄ / ethanol; diethyl ether; tetrahydrofuran / 0.33 h / 0 °C

2.1: 24 mg / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 6 h / Heating

3.1: 81 percent / pyridine; AcOH; NaH₂PO₃*H₂O / Raney nickel / H₂O / 6 h / 50 °C

4.1: tetrahydrofuran / 0.5 h / 0 °C

5.1: triphenylphosphine; diisopropyl azodicarboxylate / diethyl ether / 10 h / 20 °C

6.1: 7.8 mg / potassium carbonate / ethanol / 5 h / 20 °C

7.1: 98 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

8.1: 95 percent / aq. lithium hydroxide / tetrahydrofuran; methanol / 6 h / 20 °C

9.1: 80 percent / DCC; HOBt / 24 h / 0 - 20 °C

10.1: 96 percent / aq. lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C

11.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

12.1: 80 percent / aq. potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 20 °C

13.1: DIPEA; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2.5 h / 20 °C

13.2: 82 percent / DMAP / benzene / 8 h

14.1: 90 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; lithium borohydride; sodium dihydrogen phosphate; di-isopropyl azodicarboxylate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 2.1: Mitsunobu reaction / 5.1: Mitsunobu reaction;

DOI:10.1021/ol070855h

upstream raw materials:

jaspamide Z₁

(R)-3-((R)-3-(2-Bromo-1H-indol-3-yl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-methoxymethoxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine ρ-lactone

C₄₅H₆₅N₄O₆SiBr

Downstream raw materials:

Acetic acid 4-[(E)-7-(2-bromo-1H-indol-3-ylmethyl)-8,10,13,15,17,19-hexamethyl-2,6,9,12-tetraoxo-1-oxa-5,8,11-triaza-cyclononadec-15-en-4-yl]-phenyl ester

(E)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid [1-({2-(2-bromo-1H-indol-3-yl)-1-[3-hydroxy-1-(4-hydroxy-phenyl)-propylcarbamoyl]-ethyl}-methyl-carbamoyl)-ethyl]-amide

jaspamide Z₁

Refernces

A Stereoselective Synthesis of Trisubstituted Alkenes. Part 2. The Nickel-catalysed Coupling of Grignard Reagents with 5-Alkyl-3,4-dihydro-2H-pyrans and Acyclic Enol Ethers

10.1039/P19920003431

The study investigates the nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans and acyclic enol ethers to produce trisubstituted alkenes with high stereoselectivity and retention of configuration. The key chemicals involved include various Grignard reagents (such as MeMgBr, PhMgBr, and BuMgBr), 6-alkyl-3,4-dihydro-2H-pyrans (like 6-pentyl-3,4-dihydro-2H-pyran and 6-isobutyl-3,4-dihydro-2H-pyran), and acyclic enol ethers. The study explores different methods for preparing the dihydropyrans and examines the scope and stereochemistry of the coupling reactions, finding that dihydropyrans are less reactive than dihydrofurans but still provide valuable routes to functionalized trisubstituted alkenes. The research also includes applications of the coupling reactions in the synthesis of natural product fragments, such as the aggregation pheromone of the square-necked grain beetle, a fragment of Premonensin B, and the polyketide fragment of Jaspamide.

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