136660-70-3
Chemical Structure
Plusbacin A3
- CAS No.: 136660-70-3
- Formula:C50H83N11O20
- Molecular Weight:1158.26
InChIKey: HFPVTZNYHFSJMC-KPVYVAMXSA-N
SMILES: O=C1[C@@]2([H])N(CC[C@@H]2O)C([C@H](NC([C@@](NC([C@@H](NC([C@@]3([H])N(C([C@H](NC([C@@](NC(C[C@H](OC([C@](N1)([H])[C@H](O)C(O)=O)=O)CCCCCCCCCCC(C)C)=O)([H])[C@H](O)C)=O)C)=O)CC[C@@H]3O)=O)CCCNC(N)=N)=O)([H])[C@@H](O)C(O)=O)=O)CO)=O
Biological Activity: Plusbacin A3 is a cyclic lipodepsipeptide isolated from Pseudomonas sp. PB-6250 that inhibits bacterial cell wall biosynthesis and disrupts membrane integrity. Plusbacin A3 binds lipid intermediates, blocking transglycosylation and lipid intermediate formation in peptidoglycan synthesis. Plusbacin A3 inhibits teichoic acid biosynthesis. Plusbacin A3 exhibits activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci, with low susceptibility to resistance, and is inactive against Gram-negative bacteria. Plusbacin A3 can be used in research on bacterial infections[1][2][3][4][5][6].
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Plusbacin A3 | Plusbacin A3 is a cyclic lipodepsipeptide isolated from Pseudomonas sp. PB-6250 that inhibits bacterial cell wall biosynthesis and disrupts membrane integrity. Plusbacin A3 binds lipid intermediates, blocking transglycosylation and lipid intermediate formation in peptidoglycan synthesis. Plusbacin A3 inhibits teichoic acid biosynthesis. Plusbacin A3 exhibits activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci, with low susceptibility to resistance, and is inactive against Gram-negative bacteria. Plusbacin A3 can be used in research on bacterial infections. | |||||||||||||||||||||
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References
- [1]. Katsuyama A, et al. Total Synthesis and Antibacterial Investigation of Plusbacin A. Organic letters. 2017 Jul 21;19(14):3771-3774.
- [2]. Kim SJ, et al. The isotridecanyl side chain of plusbacin-A3 is essential for the transglycosylase inhibition of peptidoglycan biosynthesis. Biochemistry. 2013 Mar 19;52(11):1973-9.
- [3]. Wohlrab A, et al. Total synthesis of plusbacin A3: a depsipeptide antibiotic active against vancomycin-resistant bacteria. J Am Chem Soc. 2007 Apr 11;129(14):4175-7.
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[4]. Kumar G, et al. Natural products acting against S. aureus through membrane and cell wall disruption. Nat Prod Rep. 2023 Oct 18;40(10):1608-1646.
- [5]. Maki H, et al. Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus. Antimicrobial agents and chemotherapy. 2001 Jun;45(6):1823-7.
- [6]. O'Connor RD, et al. Dual Mode of Action for Plusbacin A in Staphylococcus aureus. The journal of physical chemistry. B. 2017 Feb 23;121(7):1499-1505.
