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MedKoo Cat#: 596733 | Name: Pseudobactin

Description:

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

Pseudobactin is a linear hexapeptide fluorescent iron transport agent (siderophore) from plant growth promoter Pseudomonas B10.

Chemical Structure

Pseudobactin
Pseudobactin
CAS#76975-04-7

Theoretical Analysis

MedKoo Cat#: 596733

Name: Pseudobactin

CAS#: 76975-04-7

Chemical Formula: C42H60N12O16

Exact Mass: 988.4250

Molecular Weight: 989.01

Elemental Analysis: C, 51.01; H, 6.12; N, 17.00; O, 25.88

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Pseudobactin; Ferric pseudobactin;
IUPAC/Chemical Name
(3R)-4-(((S)-1-(((2R,3R)-1-(((S)-1-amino-1-oxopropan-2-yl)((R)-1-hydroxy-2-oxopiperidin-3-yl)amino)-3-hydroxy-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)amino)-3-((S)-2-amino-6-((S)-5-(4-amino-4-oxobutanamido)-8,9-dihydroxy-2,3-dihydro-1H-pyrimido[1,2-a]quinoline-1-carboxamido)hexanamido)-2-hydroxy-4-oxobutanoic acid
InChi Key
HGYMGQIZTWEDBI-WBYFLIHPSA-N
InChi Code
InChI=1S/C42H60N12O16/c1-18(36(62)50-31(20(3)55)41(67)53(19(2)34(45)61)25-8-6-14-52(70)40(25)66)48-39(65)32(33(60)42(68)69)51-37(63)22(43)7-4-5-12-47-38(64)24-11-13-46-35-23(49-30(59)10-9-29(44)58)15-21-16-27(56)28(57)17-26(21)54(24)35/h15-20,22,24-25,31-33,55-57,60,70H,4-14,43H2,1-3H3,(H2,44,58)(H2,45,61)(H,47,64)(H,48,65)(H,49,59)(H,50,62)(H,51,63)(H,68,69)/t18-,19-,20+,22-,24-,25+,31+,32+,33?/m0/s1
SMILES Code
C[C@@H](C(N)=O)N(C([C@@H]([C@H](O)C)NC([C@H](C)NC([C@@H](C(O)C(O)=O)NC([C@H](CCCCNC([C@@H]1CCN=C2N1C3=C(C=C(O)C(O)=C3)C=C2NC(CCC(N)=O)=O)=O)N)=O)=O)=O)=O)[C@H]4C(N(O)CCC4)=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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 989.01 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
1: Jensen JL, Wu Q, Colbert CL. NMR assignments of the N-terminal signaling domain of the TonB-dependent outer membrane transducer PupB. Biomol NMR Assign. 2018 Apr;12(1):91-94. doi: 10.1007/s12104-017-9785-0. Epub 2017 Oct 25. PubMed PMID: 29071576; PubMed Central PMCID: PMC5871555. 2: Jensen JL, Balbo A, Neau DB, Chakravarthy S, Zhao H, Sinha SC, Colbert CL. Mechanistic Implications of the Unique Structural Features and Dimerization of the Cytoplasmic Domain of the Pseudomonas Sigma Regulator, PupR. Biochemistry. 2015 Sep 29;54(38):5867-77. doi: 10.1021/acs.biochem.5b00826. Epub 2015 Sep 14. PubMed PMID: 26313375; PubMed Central PMCID: PMC4701049. 3: Kumar R, Mittal V, Chutia P, Ramamurthy VV. Taxonomy of Fulgoraecia melanoleuca (Fletcher, 1939), (Lepidoptera: Epipyropidae) in India, a biological control agent of Pyrilla perpusilla (Walker) (Hemiptera: Lophopidae). Zootaxa. 2015 Jun 23;3974(3):431-9. doi: 10.11646/zootaxa.3974.3.10. PubMed PMID: 26249916. 4: Djavaheri M, Mercado-Blanco J, Versluis C, Meyer JM, Loon LC, Bakker PA. Iron-regulated metabolites produced by Pseudomonas fluorescens WCS374r are not required for eliciting induced systemic resistance against Pseudomonas syringae pv. tomato in Arabidopsis. Microbiologyopen. 2012 Sep;1(3):311-25. doi: 10.1002/mbo3.32. Epub 2012 Aug 24. PubMed PMID: 23170230; PubMed Central PMCID: PMC3496975. 5: De Vleesschauwer D, Djavaheri M, Bakker PA, Höfte M. Pseudomonas fluorescens WCS374r-induced systemic resistance in rice against Magnaporthe oryzae is based on pseudobactin-mediated priming for a salicylic acid-repressible multifaceted defense response. Plant Physiol. 2008 Dec;148(4):1996-2012. doi: 10.1104/pp.108.127878. Epub 2008 Oct 22. PubMed PMID: 18945932; PubMed Central PMCID: PMC2593667. 6: Duijff BJ, Recorbet G, Bakker PA, Loper JE, Lemanceau P. Microbial Antagonism at the Root Level Is Involved in the Suppression of Fusarium Wilt by the Combination of Nonpathogenic Fusarium oxysporum Fo47 and Pseudomonas putida WCS358. Phytopathology. 1999 Nov;89(11):1073-9. doi: 10.1094/PHYTO.1999.89.11.1073. PubMed PMID: 18944664. 7: de Boer M, Bom P, Kindt F, Keurentjes JJ, van der Sluis I, van Loon LC, Bakker PA. Control of Fusarium Wilt of Radish by Combining Pseudomonas putida Strains that have Different Disease-Suppressive Mechanisms. Phytopathology. 2003 May;93(5):626-32. doi: 10.1094/PHYTO.2003.93.5.626. PubMed PMID: 18942986. 8: Ferguson AD, Amezcua CA, Halabi NM, Chelliah Y, Rosen MK, Ranganathan R, Deisenhofer J. Signal transduction pathway of TonB-dependent transporters. Proc Natl Acad Sci U S A. 2007 Jan 9;104(2):513-8. Epub 2006 Dec 29. PubMed PMID: 17197416; PubMed Central PMCID: PMC1760641. 9: Maunsell B, Adams C, O'Gara F. Complex regulation of AprA metalloprotease in Pseudomonas fluorescens M114: evidence for the involvement of iron, the ECF sigma factor, PbrA and pseudobactin M114 siderophore. Microbiology. 2006 Jan;152(Pt 1):29-42. PubMed PMID: 16385113. 10: Saikia R, Srivastava AK, Singh K, Arora DK, Lee MW. Effect of Iron Availability on Induction of Systemic Resistance to Fusarium Wilt of Chickpea by Pseudomonas spp. Mycobiology. 2005 Mar;33(1):35-40. doi: 10.4489/MYCO.2005.33.1.035. Epub 2005 Mar 31. PubMed PMID: 24049472; PubMed Central PMCID: PMC3774855. 11: Meziane H, VAN DER Sluis I, VAN Loon LC, Höfte M, Bakker PA. Determinants of Pseudomonas putida WCS358 involved in inducing systemic resistance in plants. Mol Plant Pathol. 2005 Mar 1;6(2):177-85. doi: 10.1111/j.1364-3703.2005.00276.x. PubMed PMID: 20565648. 12: Budzikiewicz H. Siderophores of the Pseudomonadaceae sensu stricto (fluorescent and non-fluorescent Pseudomonas spp.). Fortschr Chem Org Naturst. 2004;87:81-237. Review. PubMed PMID: 15079896. 13: Cornelis P, Matthijs S. Diversity of siderophore-mediated iron uptake systems in fluorescent pseudomonads: not only pyoverdines. Environ Microbiol. 2002 Dec;4(12):787-98. Review. PubMed PMID: 12534462. 14: Shen J, Meldrum A, Poole K. FpvA receptor involvement in pyoverdine biosynthesis in Pseudomonas aeruginosa. J Bacteriol. 2002 Jun;184(12):3268-75. PubMed PMID: 12029043; PubMed Central PMCID: PMC135083. 15: Leoni L, Ambrosi C, Petrucca A, Visca P. Transcriptional regulation of pseudobactin synthesis in the plant growth-promoting Pseudomonas B10. FEMS Microbiol Lett. 2002 Mar 5;208(2):219-25. PubMed PMID: 11959440. 16: Devescovi G, Aguilar C, Majolini MB, Marugg J, Weisbeek P, Venturi V. A siderophore peptide synthetase gene from plant-growth-promoting Pseudomonas putida WCS358. Syst Appl Microbiol. 2001 Nov;24(3):321-30. PubMed PMID: 11822666. 17: Mercado-Blanco J, van der Drift KM, Olsson PE, Thomas-Oates JE, van Loon LC, Bakker PA. Analysis of the pmsCEAB gene cluster involved in biosynthesis of salicylic acid and the siderophore pseudomonine in the biocontrol strain Pseudomonas fluorescens WCS374. J Bacteriol. 2001 Mar;183(6):1909-20. PubMed PMID: 11222588; PubMed Central PMCID: PMC95085. 18: Ambrosi C, Leoni L, Putignani L, Orsi N, Visca P. Pseudobactin biogenesis in the plant growth-promoting rhizobacterium Pseudomonas strain B10: identification and functional analysis of the L-ornithine N(5)-oxygenase (psbA) gene. J Bacteriol. 2000 Nov;182(21):6233-8. PubMed PMID: 11029447; PubMed Central PMCID: PMC94761. 19: Marek-Kozaczuk M, Kopcińska J, Lotocka B, Golinowski W, Skorupska A. Infection of clover by plant growth promoting Pseudomonas fluorescens strain 267 and Rhizobium leguminosarum bv. trifolii studied by mTn5-gusA. Antonie Van Leeuwenhoek. 2000 Jul;78(1):1-11. PubMed PMID: 11016690. 20: Vossen W, Fuchs R, Taraz K, Budzikiewicz H. Can the peptide chain of a pyoverdin be bound by an ester bond to the chromophore?--The old problem of pseudobactin 7SR1. Z Naturforsch C. 2000 Mar-Apr;55(3-4):153-64. PubMed PMID: 10817203.

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