cyclo[OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-Val]

Base Information

• Chemical Name: cyclo[OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-Val]
• CAS No.: 2001-95-8
• Deprecated CAS: 11005-80-4,134-16-7,32398-05-3
• Molecular Formula: C54H90 N6 O18
• Molecular Weight: 1111.34
• Hs Code.: 29419090
• European Community (EC) Number: 217-896-6
• UN Number: 2811,2588
• Metabolomics Workbench ID: 51757
• NCI Thesaurus Code: C924
• Wikipedia: Valinomycin
• Mol file: 2001-95-8.mol

Synonyms:Valinomycin

Chemical Property of cyclo[OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-Val]

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 186-190 °C
• Refractive Index: 1.448
• Boiling Point: 1321.6 °C at 760 mmHg
• PKA: 11.32±0.70(Predicted)
• Flash Point: 753.1 °C
• PSA: 332.40000
• Density: 1.060
• LogP: 4.31610
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10 mg/mL
• Water Solubility.: Soluble in DMSO at 10mg/ml. Insoluble in water
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 9
• Exact Mass: 1110.63116004
• Heavy Atom Count: 78
• Complexity: 1910
• Transport DOT Label: Poison

Purity/Quality:

98%, ^*data from raw suppliers

Valinomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,T+,Xi
• Statements: 27/28-36/37/38-21/22
• Safety Statements: 36-45-36/37-28-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@H](C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C
• Description: Valinomycin (2001-95-8) is a selective K+ ionophore capable of transporting potassium ions through lipid membranes.1 Valinomycin can induce apoptosis in cells by causing a rapid loss of mitochondrial membrane potential via potassium efflux.2,3
• Uses: Insecticide, nematocide, Patterson, Wright, US 3520973 (1970 to Am. Cyanamid). antibiotic; LD50 (rat, po) 4 mg/kg K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and anta gonizes ET-induced vasoconstriction. Used as insecticide, nematocide. Valinomycin is a hydrophobic cyclodepsipeptide with potent antitumour activity. Valinomycin is a highly selective potassium ionophore and this action leads to a diverse range of profound cell membrane effects. More recently, valinomycin has found application as a biosensor to detect to detect potassium efflux. Valinomycin is a hydrophobic cyclodepsipeptide with potent antitumor activity. Valinomycin is a highly selective potassium ionophore and this action leads to a diverse range of profound cell membrane effects. More recently, valinomycin has found application as a biosensor to detect to detect potassium efflux.

Technology Process of cyclo[OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-Val]

There total 3 articles about cyclo[OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-D-Val-OAla-Val-D-OVal-Val] 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:

D-Hiv-D-Val-L-Lac-L-Val-SNAC → valinomycin (2001-95-8,11005-80-4)

Guidance literature:

With recombinant terminal CesB thioesterase; In aq. buffer; at 22 ℃; for 14h; pH=7.4; Enzymatic reaction;

DOI:10.1021/acs.jnatprod.0c00333

Reference yield:

TFA.(D-Val-Lac-Val-D-Hyv)3-OH (126784-73-4) → valinomycin (2001-95-8,11005-80-4)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81083-8

Reference yield:

Boc-(D-Val-Lac-Val-D-Hyv)3-OH → valinomycin (2001-95-8,11005-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.5 h

2: 107 mg / BOP, TEA / CH₂Cl₂ / 48 h / Ambient temperature

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81083-8

upstream raw materials:

TFA_.(D-Val-Lac-Val-D-Hyv)3-OH

Downstream raw materials:

(3S,6S)-3-isopropyl-6-methyl-morpholine-2,5-dione

C₅₄H₉₀N₆O₁₈*C₁₈H₂₁N₂O^(1-)*K⁽¹⁺⁾

Refernces

• 1、 Zeggaf, Choukri,Poncet, Joel,Jouin, Patrick,Dufour, Marie-Noelle,Castro, Bertrand. "ISOPROPENYL CHLOROCARBONATE (IPCC) IN AMINO ACID AND PEPTIDE CHEMISTRY: ESTERIFICATION OF N-PROTECTED AMINO ACIDS; APPLICATION TO THE SYNTHESIS OF THE DEPSIPEPTIDE VALINOMYCIN". . p. 5039 - 5050. Retrieved 2007/10/02.