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MedKoo Cat#: 145763 | Name: Platencin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Platencin is a natural product and a potent antibiotic that was originally isolated from Streptomyces platensis. It acts by inhibiting the bacterial fatty acid synthesis pathway, specifically targeting the enzymes involved in the biosynthesis of fatty acids, which are essential for bacterial cell membrane integrity. Platencin has demonstrated activity against various Gram-positive bacteria, including some that are resistant to other antibiotics. Due to its unique mechanism of action, platencin has garnered interest in the development of new antibiotics, especially in the face of increasing antibiotic resistance.

Chemical Structure

Platencin
Platencin
CAS#869898-86-2

Theoretical Analysis

MedKoo Cat#: 145763

Name: Platencin

CAS#: 869898-86-2

Chemical Formula: C24H27NO6

Exact Mass: 425.1800

Molecular Weight: 425.48

Elemental Analysis: C, 67.75; H, 6.40; N, 3.29; O, 22.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Platencin;
IUPAC/Chemical Name
2,4-dihydroxy-3-(3-((2S,4aS,8S,8aR)-8-methyl-3-methylene-7-oxo-1,3,4,7,8,8a-hexahydro-2H-2,4a-ethanonaphthalen-8-yl)propanamido)benzoic acid
InChi Key
DWUHGPPFFABTIY-RLWZQHMASA-N
InChi Code
1S/C24H27NO6/c1-13-12-24-9-5-14(13)11-17(24)23(2,18(27)6-10-24)8-7-19(28)25-20-16(26)4-3-15(21(20)29)22(30)31/h3-4,6,10,14,17,26,29H,1,5,7-9,11-12H2,2H3,(H,25,28)(H,30,31)/t14-,17-,23-,24+/m0/s1
SMILES Code
[H][C@@]12C[C@@H]3CC[C@]1(CC3=C)C=CC(=O)[C@@]2(C)CCC(=O)NC4=C(O)C=CC(C(O)=O)=C4O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 425.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rudolf JD, Dong LB, Shen B. Platensimycin and platencin: Inspirations for chemistry, biology, enzymology, and medicine. Biochem Pharmacol. 2017 Jun 1;133:139-151. doi: 10.1016/j.bcp.2016.11.013. Epub 2016 Nov 16. PMID: 27865713; PMCID: PMC5410400. 2: Shang R, Liang J, Yi Y, Liu Y, Wang J. Review of Platensimycin and Platencin: Inhibitors of β-Ketoacyl-acyl Carrier Protein (ACP) Synthase III (FabH). Molecules. 2015 Sep 3;20(9):16127-41. doi: 10.3390/molecules200916127. PMID: 26404223; PMCID: PMC6332302. 3: Martens E, Demain AL. Platensimycin and platencin: promising antibiotics for future application in human medicine. J Antibiot (Tokyo). 2011 Nov;64(11):705-10. doi: 10.1038/ja.2011.80. Epub 2011 Sep 14. PMID: 21915133. 4: Allahverdiyev AM, Bagirova M, Abamor ES, Ates SC, Koc RC, Miraloglu M, Elcicek S, Yaman S, Unal G. The use of platensimycin and platencin to fight antibiotic resistance. Infect Drug Resist. 2013 Sep 18;6:99-114. doi: 10.2147/IDR.S25076. PMID: 24082790; PMCID: PMC3785399. 5: Palanichamy K, Kaliappan KP. Discovery and syntheses of "superbug challengers"-platensimycin and platencin. Chem Asian J. 2010 Apr 1;5(4):668-703. doi: 10.1002/asia.200900423. PMID: 20209576. 6: Qiu L, Wen Z, Li Y, Tian K, Deng Y, Shen B, Duan Y, Huang Y. Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions. Org Biomol Chem. 2019 Apr 24;17(17):4261-4272. doi: 10.1039/c9ob00324j. PMID: 30816397. 7: Li Y, Weng X, Deng Y, Pan J, Zhu S, Wen Z, Yuan Y, Li S, Shen B, Duan Y, Huang Y. Semisynthesis and Biological Evaluation of Platencin Thioether Derivatives: Dual FabF and FabH Inhibitors against MRSA. ACS Med Chem Lett. 2021 Feb 15;12(3):433-442. doi: 10.1021/acsmedchemlett.0c00653. PMID: 33738071; PMCID: PMC7957939. 8: Smanski MJ, Peterson RM, Rajski SR, Shen B. Engineered Streptomyces platensis strains that overproduce antibiotics platensimycin and platencin. Antimicrob Agents Chemother. 2009 Apr;53(4):1299-304. doi: 10.1128/AAC.01358-08. Epub 2009 Jan 21. PMID: 19164156; PMCID: PMC2663125. 9: Wang J, Kodali S, Lee SH, Galgoci A, Painter R, Dorso K, Racine F, Motyl M, Hernandez L, Tinney E, Colletti SL, Herath K, Cummings R, Salazar O, González I, Basilio A, Vicente F, Genilloud O, Pelaez F, Jayasuriya H, Young K, Cully DF, Singh SB. Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties. Proc Natl Acad Sci U S A. 2007 May 1;104(18):7612-6. doi: 10.1073/pnas.0700746104. Epub 2007 Apr 24. PMID: 17456595; PMCID: PMC1863502. 10: Qiu L, Tian K, Wen Z, Deng Y, Kang D, Liang H, Zhu X, Shen B, Duan Y, Huang Y. Biomimetic Stereoselective Sulfa-Michael Addition Leads to Platensimycin and Platencin Sulfur Analogues against Methicillin-Resistant Staphylococcus aureus. J Nat Prod. 2018 Feb 23;81(2):316-322. doi: 10.1021/acs.jnatprod.7b00745. Epub 2018 Feb 1. PMID: 29389125; PMCID: PMC6245554. 11: Dong LB, Rudolf JD, Shen B. A Mutasynthetic Library of Platensimycin and Platencin Analogues. Org Lett. 2016 Sep 16;18(18):4606-9. doi: 10.1021/acs.orglett.6b02248. Epub 2016 Sep 6. PMID: 27599271; PMCID: PMC5048679. 12: Varseev GN, Maier ME. Formal total synthesis of platencin. Angew Chem Int Ed Engl. 2009;48(20):3685-8. doi: 10.1002/anie.200900447. PMID: 19353600. 13: Defieber C, Mohr JT, Grabovyi GA, Stoltz BM. Short Enantioselective Formal Synthesis of (-)-Platencin. Synthesis (Stuttg). 2018 Nov;50(22):4359-4368. doi: 10.1055/s-0037-1610437. Epub 2018 Jul 23. PMID: 31061542; PMCID: PMC6498846. 14: Yadav JS, Goreti R, Pabbaraja S, Sridhar B. Short route to platencin. Org Lett. 2013 Jul 19;15(14):3782-5. doi: 10.1021/ol401760e. Epub 2013 Jul 8. PMID: 23834636. 15: Tiefenbacher K, Gollner A, Mulzer J. Syntheses and antibacterial properties of iso-platencin, Cl-iso-platencin and Cl-platencin: identification of a new lead structure. Chemistry. 2010 Aug 16;16(31):9616-22. doi: 10.1002/chem.201000706. PMID: 20486112. 16: Chang EL, Schwartz BD, Draffan AG, Banwell MG, Willis AC. A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin. Chem Asian J. 2015 Feb;10(2):427-39. doi: 10.1002/asia.201403069. Epub 2014 Nov 13. PMID: 25393231. 17: Nicolaou KC, Tria GS, Edmonds DJ, Kar M. Total syntheses of (+/-)-platencin and (-)-platencin. J Am Chem Soc. 2009 Nov 4;131(43):15909-17. doi: 10.1021/ja906801g. PMID: 19824676; PMCID: PMC2783895. 18: Fluegel LL, Deng MR, Su P, Kalkreuter E, Yang D, Rudolf JD, Dong LB, Shen B. Development of platensimycin, platencin, and platensilin overproducers by biosynthetic pathway engineering and fermentation medium optimization. J Ind Microbiol Biotechnol. 2024 Jan 9;51:kuae003. doi: 10.1093/jimb/kuae003. PMID: 38262768; PMCID: PMC10847714. 19: Gupta S, Undale VR, Lakhadive K. Novel Targets for Antimicrobials. Turk J Pharm Sci. 2020 Oct;17(5):565-575. doi: 10.4274/tjps.galenos.2020.90197. Epub 2020 Oct 30. PMID: 33177939; PMCID: PMC7650728. 20: Gao ZX, Wang H, Su AH, Li QY, Liang Z, Zhang YQ, Liu XY, Zhu MZ, Zhang HX, Hou YT, Li X, Sun LR, Li J, Xu ZJ, Lou HX. Asymmetric Synthesis and Biological Evaluation of Platensilin, Platensimycin, Platencin, and Their Analogs via a Bioinspired Skeletal Reconstruction Approach. J Am Chem Soc. 2024 Jul 17;146(28):18967-18978. doi: 10.1021/jacs.4c02256. Epub 2024 Jul 8. PMID: 38973592.

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