Luzopeptin A

Base Information

• Chemical Name: Luzopeptin A
• CAS No.: 75580-37-9
• Deprecated CAS: 85255-31-8
• Molecular Formula: C₆₄H₇₈N₁₄O₂₄
• Molecular Weight: 1427.4
• DSSTox Substance ID: DTXSID401317872
• Metabolomics Workbench ID: 98229
• Nikkaji Number: J1.024.363G
• Wikidata: Q105224279
• Mol file: 75580-37-9.mol

Synonyms:antibiotic BBM 928C;BBM 928A;BBM 928C;BBM-928 A;BBM-928 C;BBM-928A;BBM-928C;luzopeptin;luzopeptin A;luzopeptin B;luzopeptin C;luzopeptins

Chemical Property of Luzopeptin A

Chemical Property:

• PKA: 6.75±0.40(Predicted)
• PSA: 493.34000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: -3.47180
• Solubility.: Soluble in DMSO;Soluble in dimethyl formamide
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 28
• Rotatable Bond Count: 12
• Exact Mass: 1426.53133941
• Heavy Atom Count: 102
• Complexity: 3020

Purity/Quality:

98%Min ^*data from raw suppliers

Luzopeptin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC=NN2C1C(=O)NCC(=O)N(CC(=O)N(C(C(=O)OCC(C(=O)N3C(C(CC=N3)OC(=O)C)C(=O)NCC(=O)N(CC(=O)N(C(C(=O)OCC(C2=O)NC(=O)C4=C(C=C5C=C(C=CC5=N4)OC)O)C(C)(C)O)C)C)NC(=O)C6=C(C=C7C=C(C=CC7=N6)OC)O)C(C)(C)O)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC=NN2[C@@H]1C(=O)NCC(=O)N(CC(=O)N([C@H](C(=O)OC[C@H](C(=O)N3[C@@H]([C@H](CC=N3)OC(=O)C)C(=O)NCC(=O)N(CC(=O)N([C@H](C(=O)OC[C@H](C2=O)NC(=O)C4=C(C=C5C=C(C=CC5=N4)OC)O)C(C)(C)O)C)C)NC(=O)C6=C(C=C7C=C(C=CC7=N6)OC)O)C(C)(C)O)C)C
• Uses: Luzopeptin A is a member of the echinomycin (quinomycin A) class of antitumor and antibiotic agents that act by forming a stable DNA complex by bis-intercalation. Luzopeptin A is alsoa potent inhibitor of HIV-1 reverse transcriptase. Luzopeptin A is a cyclic depsipeptide antibiotic first isolated from an actinomycete strain. It displays antitumor activity, as it is highly active in mice against a variety of experimental tumors. Luzopeptin A acts as a bifunctional DNA intercalator that strongly binds DNA and forms crosslinks between DNA molecules. It also inhibits reverse transcriptases from HIV-1 and HIV-2 (IC50s = 7 and 68 nM, respectively), as well as cellular DNA polymerases.[Cayman Chemical] Luzopeptin A is an inhibitor of HIV-1 and HIV-2 reverse transcriptase.

Technology Process of Luzopeptin A

There total 1 articles about Luzopeptin 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: 50.0%

acetic anhydride (108-24-7) + luzopeptin C (76110-01-5) → luzopeptin B (76149-24-1) + luzopeptin A (75580-37-9)

Guidance literature:

With pyridine; sodium carbonate; Yield given; Multistep reaction; 1.) 23 deg C, 7 h, 2.) THF, MeOH, 23 deg C, 50 min;

DOI:10.1021/ja983925b

upstream raw materials:

acetic anhydride

luzopeptin C

Refernces

(-)-sandramycin: Total synthesis and preliminary DNA binding properties

10.1021/ja00077a082

The research focuses on the total synthesis of (-)-sandramycin, a potent antitumor antibiotic, and an investigation into its preliminary DNA binding properties. The purpose of this study was to confirm the structure and absolute stereochemistry of sandramycin and to report on its high-affinity, bifunctional intercalation with DNA. The researchers achieved the first total synthesis of a member of this class of naturally occurring agents, which could lead to the development of analogs with modified intercalation capabilities. Key chemicals used in the synthesis process included BOC-Gly-Sar-OH, D-N-Me-val-oCH2l, DCC, DMAP, EDCI, HOBt, NaHCO3, and various other reagents for coupling reactions, deprotection steps, and cyclization. The conclusions drawn from the study indicated that (-)-sandramycin possesses a binding constant comparable to luzopeptin A, binds with higher selectivity, and induces the unwinding of negatively supercoiled DNA and its rewinding at lower agent concentrations than luzopeptin A.

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