Friulimicin B

• CAT Number: I027798
• CAS Number: 239802-15-4
• Molecular Formula: C59H94N14O19
• Molecular Weight: 1303.48
• Purity: 98%
• Synonyms: Friulimicin B
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2,2'-((6S,9R,15S,21S,24S,26aR,33S,34S,36aS)-33-((S)-4-amino-2-((Z)-12-methyltridec-3-enamido)-4-oxobutanamido)-9-((R)-1-aminoethyl)-24-((S)-1-carboxyethyl)-6-isopropyl-34-methyl-5,8,11,14,17,20,23,26,32,36-decaoxotetratriacontahydro-1H,5H-pyrido[1,2-a]pyrrolo[1,2-y][1,4,7,10,13,16,19,22,25,28]decaazacyclohentriacontine-15,21-diyl)diacetic acid
• InChI: InChI=1S/C59H94N14O19/c1-30(2)19-14-12-10-8-9-11-13-15-22-41(75)65-35(25-40(61)74)52(84)71-49-34(7)64-53(85)39-21-18-24-73(39)57(89)46(31(3)4)69-56(88)48(33(6)60)68-43(77)29-63-50(82)36(26-44(78)79)66-42(76)28-62-51(83)37(27-45(80)81)67-55(87)47(32(5)59(91)92)70-54(86)38-20-16-17-23-72(38)58(49)90/h13,15,30-39,46-49H,8-12,14,16-29,60H2,1-7H3,(H2,61,74)(H,62,83)(H,63,82)(H,64,85)(H,65,75)(H,66,76)(H,67,87)(H,68,77)(H,69,88)(H,70,86)(H,71,84)(H,78,79)(H,80,81)(H,91,92)/b15-13-/t32-,33+,34-,35-,36-,37-,38+,39-,46-,47-,48+,49-/m0/s1
• InChIKey: HVYFVLAUKMGKHL-USKUEUQVSA-N
• SMILES: C1(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)C/C=CCCCCCCCC(C)C)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3N1CCCC3)[C@@H](C(=O)O)C)CC(=O)O)CC(=O)O)[C@H](N)C)[C@@H](C)C)CCC2)C

Friulimicin B is a peptidoglycan synthesis inhibitor that is isolated from Actinoplanes friuliensis.
It is a naturally occurring cyclic lipopeptide, with excellent activity against gram-positive pathogens through cell wall interruption, including multidrug-resistant strains. Friulimicin is water soluble and amphiphilic, with an overall negative charge. .

Reference

1: Wecke T, Zühlke D, Mäder U, Jordan S, Voigt B, Pelzer S, Labischinski H, Homuth G, Hecker M, Mascher T. Daptomycin versus Friulimicin B: in-depth profiling of Bacillus subtilis cell envelope stress responses. Antimicrob Agents Chemother. 2009 Apr;53(4):1619-23. doi: 10.1128/AAC.01046-08. Epub 2009 Jan 21. PubMed PMID: 19164157; PubMed Central PMCID: PMC2663105.
2: Schneider T, Gries K, Josten M, Wiedemann I, Pelzer S, Labischinski H, Sahl HG. The lipopeptide antibiotic Friulimicin B inhibits cell wall biosynthesis through complex formation with bactoprenol phosphate. Antimicrob Agents Chemother. 2009 Apr;53(4):1610-8. doi: 10.1128/AAC.01040-08. Epub 2009 Jan 21. PubMed PMID: 19164139; PubMed Central PMCID: PMC2663061.
3: Heinzelmann E, Berger S, Puk O, Reichenstein B, Wohlleben W, Schwartz D. A glutamate mutase is involved in the biosynthesis of the lipopeptide antibiotic friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother. 2003 Feb;47(2):447-57. PubMed PMID: 12543643; PubMed Central PMCID: PMC151761.
4: Vértesy L, Ehlers E, Kogler H, Kurz M, Meiwes J, Seibert G, Vogel M, Hammann P. Friulimicins: novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. II. Isolation and structural characterization. J Antibiot (Tokyo). 2000 Aug;53(8):816-27. PubMed PMID: 11079804.