Lysobactin | CAS#118374-47-3 | antibiotic

MedKoo Cat#: 597923 | Name: Lysobactin

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Description:

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

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.

Chemical Structure

Lysobactin

CAS#118374-47-3

Theoretical Analysis

MedKoo Cat#: 597923

Name: Lysobactin

CAS#: 118374-47-3

Chemical Formula: C58H97N15O17

Exact Mass: 1275.7187

Molecular Weight: 1276.50

Elemental Analysis: C, 54.57; H, 7.66; N, 16.46; O, 21.31

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 weeks

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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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lysobactin, produced by several genera of Gram-negative gliding bacteria found in soil, is a potent antibiotic with in vivo efficacy against Staphylococcus aureus and Streptococcus pneumoniae.

In vitro activity:

Lysobactin and sorangicin A were active against the M. abscessus complex and drug resistant clinical isolates. These natural products merit further consideration to be included in the M. abscessus drug pipeline. Reference: Microbiol Spectr. 2022 Dec 21;10(6):e0267222. https://pubmed.ncbi.nlm.nih.gov/36342177/

In vivo activity:

Lysobactin, an antibiotic isolated from a strain of Lysobacter, is 2 to 4-fold more active than vancomycin against aerobic and anaerobic Gram-positive bacteria. Included in the spectrum of lysobactin are Staphylococci, Streptococci, corynebacteria, clostridia and various other Gram-positive anaerobic bacteria. When given parenterally the compound was efficacious in systemic staphylococcal and streptococcal infections in mice. Similarly, when applied topically lysobactin was also curative in a staphylococcal wound infection in mice. Reference: J Antibiot (Tokyo). 1988 Dec;41(12):1745-51. https://pubmed.ncbi.nlm.nih.gov/3209466/

Preparing Stock Solutions

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:

1. Sullivan JR, Yao J, Courtine C, Lupien A, Herrmann J, Müller R, Behr MA. Natural Products Lysobactin and Sorangicin A Show In Vitro Activity against Mycobacterium abscessus Complex. Microbiol Spectr. 2022 Dec 21;10(6):e0267222. doi: 10.1128/spectrum.02672-22. Epub 2022 Oct 31. PMID: 36342177; PMCID: PMC9769517. 2. 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. PMID: 26683668; PMCID: PMC4817722. 3. 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. doi: 10.7164/antibiotics.41.1745. PMID: 3209466. 4. Shoji J, Hinoo H, Matsumoto K, Hattori T, Yoshida T, Matsuura S, Kondo E. Isolation and characterization of katanosins A and B. J Antibiot (Tokyo). 1988 Jun;41(6):713-8. doi: 10.7164/antibiotics.41.713. PMID: 3403364.

In vitro protocol:

In vivo protocol:

1. 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. doi: 10.7164/antibiotics.41.1745. PMID: 3209466. 2. Shoji J, Hinoo H, Matsumoto K, Hattori T, Yoshida T, Matsuura S, Kondo E. Isolation and characterization of katanosins A and B. J Antibiot (Tokyo). 1988 Jun;41(6):713-8. doi: 10.7164/antibiotics.41.713. PMID: 3403364.

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.