Mycobactin S

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

MedKoo CAT#: 597544

CAS#: 26769-11-9

Description: Mycobactin S is made from metabolic products of the acid- resistant form of Mycobacterium phlei, a tuberculosis bacillus derived originally from the cold-blooded sea turtle. Importantly, it is not based on cell wall fragments or killed bacteria. Non-pathogenic to humans, this medication modulates the immune response and is highly effective against all types of tuberculosis including lung, skeletal, bone, skin and other tissues.


Chemical Structure

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Mycobactin S
CAS# 26769-11-9

Theoretical Analysis

MedKoo Cat#: 597544
Name: Mycobactin S
CAS#: 26769-11-9
Chemical Formula: C44H69N5O10
Exact Mass: 827.5044
Molecular Weight: 828.06
Elemental Analysis: C, 63.82; H, 8.40; N, 8.46; O, 19.32

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.

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Synonym: Mycobactin S;

IUPAC/Chemical Name: (S)-4-(((S)-1-hydroxy-2-oxoazepan-3-yl)amino)-4-oxobutan-2-yl N6-hydroxy-N2-((S)-2-(2-hydroxyphenyl)-4,5-dihydrooxazole-4-carbonyl)-N6-((Z)-octadec-2-enoyl)-L-lysinate

InChi Key: DQMISKWZRFJSGS-DCLNGJSXSA-N

InChi Code: InChI=1S/C44H69N5O10/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28-40(52)48(56)29-22-21-26-36(46-41(53)37-32-58-42(47-37)34-24-18-19-27-38(34)50)44(55)59-33(2)31-39(51)45-35-25-20-23-30-49(57)43(35)54/h17-19,24,27-28,33,35-37,50,56-57H,3-16,20-23,25-26,29-32H2,1-2H3,(H,45,51)(H,46,53)/b28-17-/t33-,35-,36-,37-/m0/s1

SMILES Code: Oc1ccccc1C2=N[C@@H](CO2)C(N[C@@H](CCCCN(O)C(/C=C\CCCCCCCCCCCCCCC)=O)C(O[C@@H](C)CC(N[C@@H]3C(N(O)CCCC3)=O)=O)=O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 828.06 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

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1: Madigan CA, Martinot AJ, Wei JR, Madduri A, Cheng TY, Young DC, Layre E, Murry JP, Rubin EJ, Moody DB. Lipidomic analysis links mycobactin synthase K to iron uptake and virulence in M. tuberculosis. PLoS Pathog. 2015 Mar 27;11(3):e1004792. doi: 10.1371/journal.ppat.1004792. eCollection 2015 Mar. PubMed PMID: 25815898; PubMed Central PMCID: PMC4376628.

2: Walz AJ, Möllmann U, Miller MJ. Synthesis and studies of catechol-containing mycobactin S and T analogs. Org Biomol Chem. 2007 May 21;5(10):1621-8. Epub 2007 Apr 19. PubMed PMID: 17571193.

3: White AJ, Snow GA. Isolation of mycobactinss from various mycobacteria. The properties of mycobactin S and H. Biochem J. 1969 Mar;111(5):785-92. PubMed PMID: 5783478; PubMed Central PMCID: PMC1187608.

4: Madigan CA, Cheng TY, Layre E, Young DC, McConnell MJ, Debono CA, Murry JP, Wei JR, Barry CE 3rd, Rodriguez GM, Matsunaga I, Rubin EJ, Moody DB. Lipidomic discovery of deoxysiderophores reveals a revised mycobactin biosynthesis pathway in Mycobacterium tuberculosis. Proc Natl Acad Sci U S A. 2012 Jan 24;109(4):1257-62. doi: 10.1073/pnas.1109958109. Epub 2012 Jan 9. PubMed PMID: 22232695; PubMed Central PMCID: PMC3268331.

5: Reddy PV, Puri RV, Chauhan P, Kar R, Rohilla A, Khera A, Tyagi AK. Disruption of mycobactin biosynthesis leads to attenuation of Mycobacterium tuberculosis for growth and virulence. J Infect Dis. 2013 Oct 15;208(8):1255-65. doi: 10.1093/infdis/jit250. Epub 2013 Jun 20. PubMed PMID: 23788726.

6: Juárez-Hernández RE, Franzblau SG, Miller MJ. Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis. Org Biomol Chem. 2012 Oct 7;10(37):7584-93. doi: 10.1039/c2ob26077h. Epub 2012 Aug 16. PubMed PMID: 22895786; PubMed Central PMCID: PMC3482464.

7: Vergnolle O, Xu H, Blanchard JS. Mechanism and regulation of mycobactin fatty acyl-AMP ligase FadD33. J Biol Chem. 2013 Sep 27;288(39):28116-25. doi: 10.1074/jbc.M113.495549. Epub 2013 Aug 9. PubMed PMID: 23935107; PubMed Central PMCID: PMC3784723.

8: Lun S, Guo H, Adamson J, Cisar JS, Davis TD, Chavadi SS, Warren JD, Quadri LE, Tan DS, Bishai WR. Pharmacokinetic and in vivo efficacy studies of the mycobactin biosynthesis inhibitor salicyl-AMS in mice. Antimicrob Agents Chemother. 2013 Oct;57(10):5138-40. doi: 10.1128/AAC.00918-13. Epub 2013 Jul 15. PubMed PMID: 23856770; PubMed Central PMCID: PMC3811451.

9: Lambrecht RS, Collins MT. Inability to detect mycobactin in mycobacteria-infected tissues suggests an alternative iron acquisition mechanism by mycobacteria in vivo. Microb Pathog. 1993 Mar;14(3):229-38. PubMed PMID: 8321124.

10: REICH CV, HANKS JH. USE OF ARTHROBACTER TERREGENS FOR BIOASSAY OF MYCOBACTIN. J Bacteriol. 1964 Jun;87:1317-20. PubMed PMID: 14188708; PubMed Central PMCID: PMC277205.

11: Lambrecht RS, Collins MT. Mycobacterium paratuberculosis. Factors that influence mycobactin dependence. Diagn Microbiol Infect Dis. 1992 Mar-Apr;15(3):239-46. PubMed PMID: 1582168.

12: ANTOINE AD, MORRISON NE, HANKS JH. SPECIFICITY OF IMPROVED METHODS FOR MYCOBACTIN BIOASSAY BY ARTHROBACTER TERREGENS. J Bacteriol. 1964 Dec;88:1672-7. PubMed PMID: 14240956; PubMed Central PMCID: PMC277472.

13: MORRISON NE. CIRCUMVENTION OF THE MYCOBACTIN REQUIREMENT OF MYCOBACTERIUM PARATUBERCULOSIS. J Bacteriol. 1965 Mar;89:762-7. PubMed PMID: 14273658; PubMed Central PMCID: PMC277534.

14: McMahon MD, Rush JS, Thomas MG. Analyses of MbtB, MbtE, and MbtF suggest revisions to the mycobactin biosynthesis pathway in Mycobacterium tuberculosis. J Bacteriol. 2012 Jun;194(11):2809-18. doi: 10.1128/JB.00088-12. Epub 2012 Mar 23. PubMed PMID: 22447909; PubMed Central PMCID: PMC3370630.

15: Kato L. Absence of mycobactin in Mycobacterium leprae; probably a microbe dependent microorganism implications. Indian J Lepr. 1985 Jan-Mar;57(1):58-70. PubMed PMID: 3897405.

16: Andres Y, MacCordick HJ, Hubert JC. Complexes of mycobactin from Mycobacterium smegmatis with scandium, yttrium and lanthanum. Biol Met. 1991;4(4):207-10. PubMed PMID: 1777355.

17: LaMarca BB, Zhu W, Arceneaux JE, Byers BR, Lundrigan MD. Participation of fad and mbt genes in synthesis of mycobactin in Mycobacterium smegmatis. J Bacteriol. 2004 Jan;186(2):374-82. PubMed PMID: 14702306; PubMed Central PMCID: PMC305775.

18: Quadri LE, Sello J, Keating TA, Weinreb PH, Walsh CT. Identification of a Mycobacterium tuberculosis gene cluster encoding the biosynthetic enzymes for assembly of the virulence-conferring siderophore mycobactin. Chem Biol. 1998 Nov;5(11):631-45. PubMed PMID: 9831524.

19: Luo M, Fadeev EA, Groves JT. Mycobactin-mediated iron acquisition within macrophages. Nat Chem Biol. 2005 Aug;1(3):149-53. Epub 2005 Jul 3. PubMed PMID: 16408019.

20: Hamilton HL, Czuprynski CJ. Effects of mycobactin J and lactoferrin supplementation of drinking water on the in vivo multiplication of Mycobacterium paratuberculosis in gnotobiotic mice. Can J Vet Res. 1992 Jan;56(1):70-3. PubMed PMID: 1586898; PubMed Central PMCID: PMC1263506.