WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H597923
CAS#: 118374-47-3
Description: Lysobactin, also known as katanosin B, is a potent antibiotic with in vivo efficacy against Staphylococcus aureus and Streptococcus pneumoniae. It was previously shown to inhibit peptidoglycan (PG) biosynthesis.
Hodoodo Cat#: H597923
Name: Lysobactin
CAS#: 118374-47-3
Chemical Formula: C58H97N15O17
Exact Mass: 1,275.72
Molecular Weight: 1,276.502
Elemental Analysis: C, 54.57; H, 7.66; N, 16.46; O, 21.31
Synonym: Lysobactin; Katanosin B; Katanosin A, 7-L-isoleucine-;
IUPAC/Chemical Name: (R)-2-amino-N-((S)-1-(((3S,6S,12S,15S,18R,21S,24S,27S,28R)-6-((S)-2-amino-1-hydroxy-2-oxoethyl)-15-((S)-sec-butyl)-18-(3-guanidinopropyl)-24-((R)-1-hydroxy-2-methylpropyl)-12-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-21-isobutyl-2,5,8,11,14,17,20,23,26-nonaoxo-28-phenyl-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-27-yl)amino)-4-methyl-1-oxopentan-2-yl)-4-methylpentanamide
InChi Key: KQMKBWMQSNKASI-AVSFGBOWSA-N
InChi Code: InChI=1S/C58H97N15O17/c1-12-30(10)39-53(85)71-40(31(11)75)52(84)64-24-38(76)69-42(45(78)47(60)79)55(87)68-37(25-74)57(89)90-46(32-17-14-13-15-18-32)43(73-51(83)36(23-28(6)7)66-48(80)33(59)21-26(2)3)56(88)72-41(44(77)29(8)9)54(86)67-35(22-27(4)5)50(82)65-34(49(81)70-39)19-16-20-63-58(61)62/h13-15,17-18,26-31,33-37,39-46,74-75,77-78H,12,16,19-25,59H2,1-11H3,(H2,60,79)(H,64,84)(H,65,82)(H,66,80)(H,67,86)(H,68,87)(H,69,76)(H,70,81)(H,71,85)(H,72,88)(H,73,83)(H4,61,62,63)/t30-,31-,33+,34+,35-,36-,37-,39-,40-,41-,42-,43-,44+,45-,46+/m0/s1
SMILES Code: CC[C@@H]([C@@H]1NC([C@H](NC([C@@H](NC([C@H]([C@@H](C(C)C)O)NC([C@H]([C@@H](c2ccccc2)OC([C@@H](NC([C@H]([C@@H](C(N)=O)O)NC(CNC([C@H]([C@@H](O)C)NC1=O)=O)=O)=O)CO)=O)NC([C@@H](NC([C@@H](CC(C)C)N)=O)CC(C)C)=O)=O)=O)CC(C)C)=O)CCCNC(N)=N)=O)C
Appearance: Solid powder
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: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 1,276.50 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.
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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Lee W, Schaefer K, Qiao Y, Srisuknimit V, Steinmetz H, Müller R, Kahne D, Walker S. The Mechanism of Action of Lysobactin. J Am Chem Soc. 2016 Jan 13;138(1):100-3. doi: 10.1021/jacs.5b11807. Epub 2015 Dec 24. PubMed PMID: 26683668; PubMed Central PMCID: PMC4817722.
2: Hou J, Robbel L, Marahiel MA. Identification and characterization of the lysobactin biosynthetic gene cluster reveals mechanistic insights into an unusual termination module architecture. Chem Biol. 2011 May 27;18(5):655-64. doi: 10.1016/j.chembiol.2011.02.012. PubMed PMID: 21609846.
3: Hall EA, Kuru E, VanNieuwenhze MS. Solid-phase synthesis of lysobactin (katanosin B): insights into structure and function. Org Lett. 2012 Jun 1;14(11):2730-3. doi: 10.1021/ol300926d. Epub 2012 May 21. PubMed PMID: 22612400; PubMed Central PMCID: PMC3488444.
4: Blackburn RK, Van Breemen RB. Application of an immobilized digestive enzyme assay to measure chemical and enzymatic hydrolysis of the cyclic peptide antibiotic lysobactin. Drug Metab Dispos. 1993 Jul-Aug;21(4):573-9. PubMed PMID: 8104115.
5: Bonner DP, O'Sullivan J, Tanaka SK, Clark JM, Whitney RR. Lysobactin, a novel antibacterial agent produced by Lysobacter sp. II. Biological properties. J Antibiot (Tokyo). 1988 Dec;41(12):1745-51. PubMed PMID: 3209466.
6: Guzman-Martinez A, Lamer R, VanNieuwenhze MS. Total synthesis of lysobactin. J Am Chem Soc. 2007 May 9;129(18):6017-21. Epub 2007 Apr 14. PubMed PMID: 17432854; PubMed Central PMCID: PMC2151959.
7: Campagne JM. Total syntheses of lysobactin (katanosin B). Angew Chem Int Ed Engl. 2007;46(45):8548-52. PubMed PMID: 17943932.
8: O'Sullivan J, McCullough JE, Tymiak AA, Kirsch DR, Trejo WH, Principe PA. Lysobactin, a novel antibacterial agent produced by Lysobacter sp. I. Taxonomy, isolation and partial characterization. J Antibiot (Tokyo). 1988 Dec;41(12):1740-4. PubMed PMID: 3209465.
9: von Nussbaum F, Anlauf S, Benet-Buchholz J, Häbich D, Köbberling J, Musza L, Telser J, Rübsamen-Waigmann H, Brunner NA. Structure and total synthesis of lysobactin (katanosin B). Angew Chem Int Ed Engl. 2007;46(12):2039-42. PubMed PMID: 17211904.
10: Armaroli S, Cardillo G, Gentilucci L, Gianotti M, Tolomelli A. A new selective synthesis of the Ile-allo-Thr-Gly tripeptide fragment of lysobactin. Org Lett. 2000 Apr 20;2(8):1105-7. PubMed PMID: 10804565.
11: Bernhard F, Demel G, Soltani K, Döhren HV, Blinov V. Identification of genes encoding for peptide synthetases in the gram-negative bacterium Lysobacter sp. ATCC 53042 and the fungus Cylindrotrichum oligospermum. DNA Seq. 1996;6(6):319-30. PubMed PMID: 8988370.
12: Andersen NH, Lai XN, Hammen PK, Marschner TM. Computer-aided conformational analysis based on NOESY signal intensities. Basic Life Sci. 1990;56:95-134. Review. PubMed PMID: 2078182.
13: Cardillo G, Gentilucci L, Tolomelli A. Unusual amino acids: synthesis and introduction into naturally occurring peptides and biologically active analogues. Mini Rev Med Chem. 2006 Mar;6(3):293-304. Review. PubMed PMID: 16515468.
14: Takami H, Toyoda A, Uchiyama I, Itoh T, Takaki Y, Arai W, Nishi S, Kawai M, Shin-Ya K, Ikeda H. Complete genome sequence and expression profile of the commercial lytic enzyme producer Lysobacter enzymogenes M497-1. DNA Res. 2017 Apr 1;24(2):169-177. doi: 10.1093/dnares/dsw055. PubMed PMID: 28065880; PubMed Central PMCID: PMC5397603.
15: Hafez AM, Dudding T, Wagerle TR, Shah MH, Taggi AE, Lectka T. A multistage, one-pot procedure mediated by a single catalyst: a new approach to the catalytic asymmetric synthesis of beta-amino acids. J Org Chem. 2003 Jul 25;68(15):5819-25. PubMed PMID: 12868913.
16: Mandalapu D, Ji X, Chen J, Guo C, Liu WQ, Ding W, Zhou J, Zhang Q. Thioesterase-Mediated Synthesis of Teixobactin Analogues: Mechanism and Substrate Specificity. J Org Chem. 2018 Jul 6;83(13):7271-7275. doi: 10.1021/acs.joc.7b02462. Epub 2018 Jan 31. PubMed PMID: 29357665.