Latrunculin a

Base Information

• Chemical Name: Latrunculin a
• CAS No.: 76343-93-6
• Molecular Formula: C22H31NO5S
• Molecular Weight: 421.558
• NSC Number: 613011
• UNII: SRQ9WWM084
• DSSTox Substance ID: DTXSID90893488
• Wikipedia: Latrunculin
• Wikidata: Q4255014
• Metabolomics Workbench ID: 52696
• ChEMBL ID: CHEMBL404116
• Mol file: 76343-93-6.mol

Synonyms:LAT-A;latrunculin A

Chemical Property of Latrunculin a

Chemical Property:

• Appearance/Colour: yellow waxy solid
• Refractive Index: 1.532
• PSA: 110.16000
• Density: 1.157 g/cm³
• LogP: 4.18840
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 421.19229426
• Heavy Atom Count: 29
• Complexity: 703

Purity/Quality:

98%,99%, ^*data from raw suppliers

Latrunculin A ≥97%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)C=C(CCC=CC=C1)C
• Isomeric SMILES: C[C@H]/1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]3CSC(=O)N3)O)OC(=O)/C=C(\CC/C=C/C=C1)/C
• Description: Actin disruption is used to study cell functions in vitro (e.g., migration, endocytosis) and in vivo (e.g., tumor cell invasion). Latrunculin A is a bioactive 2-thiazolidinone macrolide derived from sponges that sequesters G-actin and prevents F-actin assembly. It binds monomeric actin with 1:1 stoichiometry and can be used to block actin polymerization both in vitro (Kd = 0.2 μM) and in cells (0.5 μM, 30 min).{ Latrunculin A (1-10 μM) causes depolymerization of tumor cell cytoskeleton within ten minutes. Overnight treatment of cells with latrunculin A (10 μM) strongly suppresses actin synthesis. Prolonged cell treatment blocks dexamethasone-induced changes in actin cytoskeleton with no effect on cell viability.
• Uses: Latrunculin A has been used as medium supplementation for A549 cells to determine the internalization mechanism of CAV9 in A549 human lung carcinoma cells. Latrunculin A, Latrunculia magnifica is a stabilizer of monomeric G-actin and polymerization inhibitor.

Technology Process of Latrunculin a

There total 37 articles about Latrunculin a 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: 80.0%

Latrunculin A Methyl Ketal (76343-89-0) → latrunculin A (76343-93-6)

Guidance literature:

With acetic acid; at 60 ℃;

DOI:10.1002/anie.200500390

Reference yield:

(R)-4-((4Z,8E,10Z)-(1R,12S,15R,17R)-17-Methoxy-5,12-dimethyl-3-oxo-2,16-dioxa-bicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-2-oxo-thiazolidine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester (128359-80-8) → latrunculin A (76343-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

2: 80 percent / aq. acetic acid / 2 h / 60 °C

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1002/chem.200601135

Reference yield:

(2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-6-((S)-3-methyl-hex-4-ynyl)-2-((R)-2-oxo-thiazolidin-4-yl)-tetrahydro-pyran-4-yl ester (861821-51-4) → latrunculin A (76343-93-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 81 percent / ethyl(diisopropyl)amine / DMAP / CH₂Cl₂ / 24 h

2.1: 70 percent / Mo[N-(tBu)(3,5-dimethylphenyl)]3 / toluene / 20 h / 80 °C

3.1: 82 percent / hydrogen / Lindlar / CH₂Cl₂ / 5 h / 750.06 Torr

4.1: 62 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

5.1: 80 percent / aq. acetic acid / 2 h / 60 °C

With pyridine; tetrabutyl ammonium fluoride; hydrogen; acetic acid; Lindlar's catalyst; tris(N-tert-butyl-3,5-dimethylanilino)molybdenum(III); In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/chem.200601135

upstream raw materials:

Latrunculin A Methyl Ketal

dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate

(R)-4-[(E)-(5R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-undec-2-en-9-ynoyl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

(2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-6-((S)-3-methyl-hex-4-ynyl)-2-((R)-2-oxo-thiazolidin-4-yl)-tetrahydro-pyran-4-yl ester

Downstream raw materials:

4-((4Z,8E,10Z)-(1R,12S,15R,17R)-17-Methoxy-5,12-dimethyl-3-oxo-2,16-dioxa-bicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-thiazolidin-2-one

4-((4Z,8E,10Z)-(1R,12R,15R,17S)-17-Methoxy-5,12-dimethyl-3-oxo-2,16-dioxa-bicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-thiazolidin-2-one

4-((4Z,8E,10Z)-(1R,12S,15R)-5,12-Dimethyl-3-oxo-2,16-dioxa-bicyclo[13.3.1]nonadeca-4,8,10,17-tetraen-17-yl)-thiazolidin-2-one

C₂₆H₃₅N₃O₅S

Refernces

• 1、 Fuerstner, Alois,Turet, Laurent. "Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis". . p. 3462 - 3466. Retrieved 2007/10/03.
• 2、 Smith III, Amos B.,Leahy, James W.,Noda, Ichio,Remiszewski, Stacy W.,Liverton, Nigel J.,Zibuck, Regina. "Total synthesis of the latrunculins". . p. 2995 - 3007. Retrieved 2007/10/02.