Pseudomonic acid C

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

MedKoo CAT#: 597941

CAS#: 71980-98-8

Description: Pseudomonic acid C is the analogue of Pseudomonic Acid D which is an antibiotic isolated from Pseudomonas fluorescens.

Chemical Structure

img
Pseudomonic acid C
CAS# 71980-98-8
Instruction

Theoretical Analysis

MedKoo Cat#: 597941
Name: Pseudomonic acid C
CAS#: 71980-98-8
Chemical Formula: C26H44O8
Exact Mass: 484.30
Molecular Weight: 484.630
Elemental Analysis: C, 64.44; H, 9.15; O, 26.41

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Pseudomonic acid C; Mupirocin calcium impurity B [EP];

IUPAC/Chemical Name: 9-(((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-((4R,5S,E)-5-hydroxy-4-methylhex-2-en-1-yl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid

InChi Key: KKMHFUKZHJOMJL-WZLBZGCNSA-N

InChi Code: InChI=1S/C26H44O8/c1-18(16-24(30)33-14-9-7-5-4-6-8-13-23(28)29)15-22-26(32)25(31)21(17-34-22)12-10-11-19(2)20(3)27/h10-11,16,19-22,25-27,31-32H,4-9,12-15,17H2,1-3H3,(H,28,29)/b11-10+,18-16+/t19-,20+,21+,22+,25-,26+/m1/s1

SMILES Code: O=C(O)CCCCCCCCOC(/C=C(C)/C[C@H]1[C@H](O)[C@H](O)[C@@H](C/C=C/[C@@H](C)[C@@H](O)C)CO1)=O

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 484.63 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Sridhar Y, Srihari P. A unified strategy for the synthesis of the C1-C14 fragment of marinolic acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis of pseudomonic acid methyl monate C. Org Biomol Chem. 2014 May 14;12(18):2950-9. doi: 10.1039/c4ob00025k. PubMed PMID: 24691713.

2: Broom NJ, Cassels R, Cheng HY, Elder JS, Hannan PC, Masson N, O'Hanlon PJ, Pope A, Wilson JM. The chemistry of pseudomonic acid. 17. Dual-action C-1 oxazole derivatives of pseudomonic acid having an extended spectrum of antibacterial activity. J Med Chem. 1996 Aug 30;39(18):3596-600. PubMed PMID: 8784459.

3: Fritz E, Fekete A, Lintelmann J, Schmitt-Kopplin P, Meckenstock RU. Isolation of two Pseudomonas strains producing pseudomonic acid A. Syst Appl Microbiol. 2009 Feb;32(1):56-64. doi: 10.1016/j.syapm.2008.11.001. Epub 2008 Dec 12. PubMed PMID: 19070447.

4: Hothersall J, Wu J, Rahman AS, Shields JA, Haddock J, Johnson N, Cooper SM, Stephens ER, Cox RJ, Crosby J, Willis CL, Simpson TJ, Thomas CM. Mutational analysis reveals that all tailoring region genes are required for production of polyketide antibiotic mupirocin by pseudomonas fluorescens: pseudomonic acid B biosynthesis precedes pseudomonic acid A. J Biol Chem. 2007 May 25;282(21):15451-61. Epub 2007 Mar 23. PubMed PMID: 17383964.

5: Sutherland R, Boon RJ, Griffin KE, Masters PJ, Slocombe B, White AR. Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use. Antimicrob Agents Chemother. 1985 Apr;27(4):495-8. PubMed PMID: 3923922; PubMed Central PMCID: PMC180082.

6: Rechsteiner T, Leisinger T. Purification of isoleucyl-tRNA synthetase from Methanobacterium thermoautotrophicum by pseudomonic acid affinity chromatography. Eur J Biochem. 1989 Apr 15;181(1):41-6. PubMed PMID: 2496983.

7: Gao SS, Hothersall J, Wu J, Murphy AC, Song Z, Stephens ER, Thomas CM, Crump MP, Cox RJ, Simpson TJ, Willis CL. Biosynthesis of mupirocin by Pseudomonas fluorescens NCIMB 10586 involves parallel pathways. J Am Chem Soc. 2014 Apr 9;136(14):5501-7. doi: 10.1021/ja501731p. Epub 2014 Mar 27. PubMed PMID: 24625190.

8: Camus C, Sebille V, Legras A, Garo B, Renault A, Le Corre P, Donnio PY, Gacouin A, Perrotin D, Le Tulzo Y, Bellissant E. Mupirocin/chlorexidine to prevent methicillin-resistant Staphylococcus aureus infections: post hoc analysis of a placebo-controlled, randomized trial using mupirocin/chlorhexidine and polymyxin/tobramycin for the prevention of acquired infections in intubated patients. Infection. 2014 Jun;42(3):493-502. doi: 10.1007/s15010-013-0581-1. Epub 2014 Jan 25. PubMed PMID: 24464791.

9: Chhibber S, Gupta P, Kaur S. Bacteriophage as effective decolonising agent for elimination of MRSA from anterior nares of BALB/c mice. BMC Microbiol. 2014 Aug 12;14:212. doi: 10.1186/s12866-014-0212-8. PubMed PMID: 25112504; PubMed Central PMCID: PMC4236609.

10: Hartman-Adams H, Banvard C, Juckett G. Impetigo: diagnosis and treatment. Am Fam Physician. 2014 Aug 15;90(4):229-35. Review. PubMed PMID: 25250996.

11: Matthijs S, Vander Wauven C, Cornu B, Ye L, Cornelis P, Thomas CM, Ongena M. Antimicrobial properties of Pseudomonas strains producing the antibiotic mupirocin. Res Microbiol. 2014 Oct;165(8):695-704. doi: 10.1016/j.resmic.2014.09.009. Epub 2014 Oct 7. PubMed PMID: 25303834.

12: Thangamani S, Younis W, Seleem MN. Repurposing ebselen for treatment of multidrug-resistant staphylococcal infections. Sci Rep. 2015 Jun 26;5:11596. doi: 10.1038/srep11596. PubMed PMID: 26111644; PubMed Central PMCID: PMC4481386.

13: Curran DP, Suh YG. Selective mono-Claisen rearrangement of carbohydrate glycals. A chemical consequence of the vinylogous anomeric effect. Carbohydr Res. 1987 Dec 31;171:161-91. PubMed PMID: 3127051.

14: Hennigan AN, Reeve JN. mRNAs in the methanogenic archaeon Methanococcus vannielii: numbers, half-lives and processing. Mol Microbiol. 1994 Feb;11(4):655-70. PubMed PMID: 7515144.

15: Vingsbo Lundberg C, Frimodt-Møller N. Efficacy of topical and systemic antibiotic treatment of meticillin-resistant Staphylococcus aureus in a murine superficial skin wound infection model. Int J Antimicrob Agents. 2013 Sep;42(3):272-5. doi: 10.1016/j.ijantimicag.2013.05.008. Epub 2013 Jul 6. PubMed PMID: 23837927.

16: González-Domínguez M, Seral C, Potel C, Sáenz Y, Álvarez M, Torres C, Castillo FJ. Genotypic and phenotypic characterization of methicillin-resistant Staphylococcus aureus (MRSA) clones with high-level mupirocin resistance. Diagn Microbiol Infect Dis. 2016 Jun;85(2):213-7. doi: 10.1016/j.diagmicrobio.2016.02.021. Epub 2016 Feb 28. PubMed PMID: 27133306.

17: Blanchard C, Brooks L, Beckley A, Colquhoun J, Dewhurst S, Dunman PM. Neomycin Sulfate Improves the Antimicrobial Activity of Mupirocin-Based Antibacterial Ointments. Antimicrob Agents Chemother. 2015 Nov 23;60(2):862-72. doi: 10.1128/AAC.02083-15. Print 2016 Feb. PubMed PMID: 26596945; PubMed Central PMCID: PMC4750660.

18: Shiozawa H, Kagasaki T, Torikata A, Tanaka N, Fujimoto K, Hata T, Furukawa Y, Takahashi S. Thiomarinols B and C, new antimicrobial antibiotics produced by a marine bacterium. J Antibiot (Tokyo). 1995 Aug;48(8):907-9. PubMed PMID: 7592043.

19: Shields JA, Rahman AS, Arthur CJ, Crosby J, Hothersall J, Simpson TJ, Thomas CM. Phosphopantetheinylation and specificity of acyl carrier proteins in the mupirocin biosynthetic cluster. Chembiochem. 2010 Jan 25;11(2):248-55. doi: 10.1002/cbic.200900565. PubMed PMID: 20013982.

20: Russell D, Beekmann SE, Polgreen PM, Rubin Z, Uslan DZ. Routine Use of Contact Precautions for Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococcus: Which Way Is the Pendulum Swinging? Infect Control Hosp Epidemiol. 2016 Jan;37(1):36-40. doi: 10.1017/ice.2015.246. Epub 2015 Oct 21. PubMed PMID: 26486272.