Platencin

Base Information

• Chemical Name: Platencin
• CAS No.: 869898-86-2
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• UNII: XK356W8OOB
• ChEMBL ID: CHEMBL1092943
• Metabolomics Workbench ID: 106309
• Nikkaji Number: J2.462.373D
• Wikidata: Q27136732
• Mol file: 869898-86-2.mol

Synonyms:platencin

Chemical Property of Platencin

Chemical Property:

• Boiling Point: 670.1±55.0 °C(Predicted)
• PKA: 2.14±0.13(Predicted)
• Density: 1.38±0.1 g/cm3(Predicted)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 836

Purity/Quality:

98%Min ^*data from raw suppliers

Platencin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC3CCC2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O
• Isomeric SMILES: C[C@@]1([C@@H]2C[C@@H]3CC[C@]2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O
• Description: Platencin is a natural, broad spectrum Gram-positive antibiotic isolated from S. platensis, which is also the source of platensimycin . Platencin inhibits two key enzymes in bacterial fatty acid synthesis, β-ketoacyl-ACP synthases II and III (FabF and FabH, respectively), unlike platensimycin which only targets FabF. The IC50 values for platencin against FabF and FabH are 1.95 and 3.91 μg/ml, respectively. It does not exhibit cross-resistance to antibiotic resistant bacterial strains, including methicillin-resistant S. aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococci. For these reasons, platencin has potential applications in fighting antibiotic resistant bacteria.
• Uses: Platencin is a potent antibiotic that targets FabF and FabH proteins. Platencin is a novel, broad spectrum, Gram-positive antibiotic produced by strains of Streptomyces platensis. Platencin is more potent than its analogue, platensimycin. Platencin shows potent in vivo efficacy without any observed toxicity. Platencin targets two essential proteins, b-ketoacyl-acyl carrier protein (ACP) synthase II (FabF) and III (FabH) whereas platensimycin targets only FabF.

Technology Process of Platencin

There total 70 articles about Platencin 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%

platencin 2-(trimethylsilyl)ethyl ester (1020070-63-6) → (-)-platencin (869898-86-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 40 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/anie.200800066

Reference yield: 85.0%

C29H39NO6Si (1265279-45-5) → C24H27NO6 (1265278-78-1,869898-86-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; HATU; In N,N-dimethyl-formamide; at 23 - 40 ℃; for 1.33333h; Inert atmosphere;

DOI:10.1002/ejoc.201001281

Reference yield: 62.0%

3-amino-2,4-dihydroxybenzoic acid (860505-23-3) + 3-[(1RS,5RS,6SR,8RS)-5-methyl-9-methylidene-4-oxotricyclo[6.2.2.0(1,6)]dodec-2-en-5-yl]propanoic acid → (±)-platencin (869898-86-2)

Guidance literature:

3-[(1RS,5RS,6SR,8RS)-5-methyl-9-methylidene-4-oxotricyclo[6.2.2.0(1,6)]dodec-2-en-5-yl]propanoic acid; With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; at 20 ℃; for 7h; Inert atmosphere;

3-amino-2,4-dihydroxybenzoic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 38h; Inert atmosphere;

DOI:10.1002/anie.200800756

upstream raw materials:

platencin 2-(trimethylsilyl)ethyl ester

3-amino-2,4-dihydroxybenzoic acid

3-[(1S,5S,6R,8S)-5-methyl-9-methylene-4-oxotricyclo[6.2.2.0(1,6)]-dodec-2-en-5-yl]propionic acid

(1R,6S,8S)-9-methylidenetricyclo[6.2.2.0(1,6)]dodec-2-en-4-one

Refernces

• 1、 Chang, Ee Ling,Schwartz, Brett D.,Draffan, Alistair G.,Banwell, Martin G.,Willis, Anthony C.. "A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin". . p. 427 - 439. Retrieved 2015/02/05.
• 2、 Yoshimitsu, Takehiko,Nojima, Shoji,Hashimoto, Masashi,Tanaka, Tetsuaki. "Total synthesis of (±)-platencin". supporting information; experimental part. p. 3698 - 3701. Retrieved 2011/10/08.