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MedKoo Cat#: 597528 | Name: Phaseolotoxin

Description:

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

Phaseolotoxin is an exotoxin from Pseudomonas sp.; cleavage of C terminal alanine and homoarginine from phaseolotoxin leaves octicidine.

Chemical Structure

Phaseolotoxin
Phaseolotoxin
CAS#62249-77-8

Theoretical Analysis

MedKoo Cat#: 597528

Name: Phaseolotoxin

CAS#: 62249-77-8

Chemical Formula: C15H34N9O8PS

Exact Mass: 531.1989

Molecular Weight: 531.52

Elemental Analysis: C, 33.90; H, 6.45; N, 23.72; O, 24.08; P, 5.83; S, 6.03

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
Phaseolotoxin; Phaseolotoxin A;
IUPAC/Chemical Name
N2-(((2S)-2-amino-5-(((1-sulfohydrazinyl)hydrophosphoryl)amino)pentanoyl)-L-alanyl)-N6-carbamimidoyl-L-lysine
InChi Key
ZTMBAEPVIGUFGF-DCAQKATOSA-N
InChi Code
InChI=1S/C15H34N9O8PS/c1-9(12(25)23-11(14(27)28)6-2-3-7-20-15(17)18)22-13(26)10(16)5-4-8-21-33(29)24(19)34(30,31)32/h9-11,33H,2-8,16,19H2,1H3,(H,21,29)(H,22,26)(H,23,25)(H,27,28)(H4,17,18,20)(H,30,31,32)/t9-,10-,11-/m0/s1
SMILES Code
O=C(O)[C@H](CCCCNC(N)=N)NC([C@H](C)NC([C@H](CCCNP(N(N)S(=O)(O)=O)=O)N)=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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 531.52 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: Chen L, Li P, Deng Z, Zhao C. Ornithine Transcarbamylase ArgK Plays a Dual role for the Self-defense of Phaseolotoxin Producing Pseudomonas syringae pv. phaseolicola. Sci Rep. 2015 Aug 10;5:12892. doi: 10.1038/srep12892. PubMed PMID: 26256666; PubMed Central PMCID: PMC4530439. 2: González-Villanueva L, Arvizu-Gómez JL, Hernández-Morales A, Aguilera-Aguirre S, Álvarez-Morales A. The PhtL protein of Pseudomonas syringae pv. phaseolicola NPS3121 affects the expression of both phaseolotoxin cluster (Pht) and Non-Pht encoded genes. Microbiol Res. 2014 Feb-Mar;169(2-3):221-31. doi: 10.1016/j.micres.2013.05.002. Epub 2013 Jun 24. PubMed PMID: 23806843. 3: Aguilera S, De la Torre-Zavala S, Hernández-Flores JL, Murillo J, Bravo J, Alvarez-Morales A. Expression of the gene for resistance to phaseolotoxin (argK) depends on the activity of genes phtABC in Pseudomonas syringae pv. phaseolicola. PLoS One. 2012;7(10):e46815. doi: 10.1371/journal.pone.0046815. Epub 2012 Oct 8. PubMed PMID: 23056465; PubMed Central PMCID: PMC3466206. 4: Arvizu-Gómez JL, Hernández-Morales A, Pastor-Palacios G, Brieba LG, Álvarez-Morales A. Integration Host Factor (IHF) binds to the promoter region of the phtD operon involved in phaseolotoxin synthesis in P. syringae pv. phaseolicola NPS3121. BMC Microbiol. 2011 May 4;11:90. doi: 10.1186/1471-2180-11-90. PubMed PMID: 21542933; PubMed Central PMCID: PMC3112066. 5: De la Torre-Zavala S, Aguilera S, Ibarra-Laclette E, Hernandez-Flores JL, Hernández-Morales A, Murillo J, Alvarez-Morales A. Gene expression of Pht cluster genes and a putative non-ribosomal peptide synthetase required for phaseolotoxin production is regulated by GacS/GacA in Pseudomonas syringae pv. phaseolicola. Res Microbiol. 2011 Jun;162(5):488-98. doi: 10.1016/j.resmic.2011.04.010. Epub 2011 Apr 21. PubMed PMID: 21527339. 6: Murillo J, Bardaji L, Navarro de la Fuente L, Führer ME, Aguilera S, Alvarez-Morales A. Variation in conservation of the cluster for biosynthesis of the phytotoxin phaseolotoxin in Pseudomonas syringae suggests at least two events of horizontal acquisition. Res Microbiol. 2011 Apr;162(3):253-61. doi: 10.1016/j.resmic.2010.10.011. Epub 2010 Dec 25. PubMed PMID: 21187143. 7: López-López K, Hernández-Flores JL, Cruz-Aguilar M, Alvarez-Morales A. In Pseudomonas syringae pv. phaseolicola, expression of the argK gene, encoding the phaseolotoxin-resistant ornithine carbamoyltransferase, is regulated indirectly by temperature and directly by a precursor resembling carbamoylphosphate. J Bacteriol. 2004 Jan;186(1):146-53. PubMed PMID: 14679234; PubMed Central PMCID: PMC303443. 8: Hernández-Guzmán G, Alvarez-Morales A. Isolation and characterization of the gene coding for the amidinotransferase involved in the biosynthesis of phaseolotoxin in Pseudomonas syringae pv. phaseolicola. Mol Plant Microbe Interact. 2001 Apr;14(4):545-54. PubMed PMID: 11310742. 9: Aguilera S, López-López K, Nieto Y, Garcidueñas-Piña R, Hernández-Guzmán G, Hernández-Flores JL, Murillo J, Alvarez-Morales A. Functional characterization of the gene cluster from Pseudomonas syringae pv. phaseolicola NPS3121 involved in synthesis of phaseolotoxin. J Bacteriol. 2007 Apr;189(7):2834-43. Epub 2007 Jan 19. PubMed PMID: 17237165; PubMed Central PMCID: PMC1855804. 10: Peet RC, Panopoulos NJ. Ornithine carbamoyltransferase genes and phaseolotoxin immunity in Pseudomonas syringae pv. phaseolicola. EMBO J. 1987 Dec 1;6(12):3585-91. PubMed PMID: 16453811; PubMed Central PMCID: PMC553825. 11: Peet RC, Lindgren PB, Willis DK, Panopoulos NJ. Identification and cloning of genes involved in phaseolotoxin production by Pseudomonas syringae pv. "phaseolicola". J Bacteriol. 1986 Jun;166(3):1096-105. PubMed PMID: 3011734; PubMed Central PMCID: PMC215237. 12: Bachmann AS, Xu R, Ratnapala L, Patil SS. Inhibitory effects of phaseolotoxin on proliferation of leukemia cells HL-60, K-562 and L1210 and pancreatic cells RIN-m5F. Leuk Res. 2004 Mar;28(3):301-6. PubMed PMID: 14687626. 13: Arai T, Kino K. A novel L-amino acid ligase is encoded by a gene in the phaseolotoxin biosynthetic gene cluster from Pseudomonas syringae pv. phaseolicola 1448A. Biosci Biotechnol Biochem. 2008 Nov;72(11):3048-50. Epub 2008 Nov 7. PubMed PMID: 18997422. 14: Jahn O, Sauerstein J, Reuter G. Inhibition of ornithine carbamoyltransferase from Pseudomonas syringae pv. syringae W50 by phaseolotoxin. J Basic Microbiol. 1989;29(5):315-8. PubMed PMID: 2778649. 15: Völksch B, Laplace F, Fritsche W. [Studies on the variability of the phaseolotoxin production by Pseudomonas syringae pv. phaseolicola]. Zentralbl Mikrobiol. 1984;139(2):109-18. German. PubMed PMID: 6428075. 16: Turner JG. Effect of phaseolotoxin on the synthesis of arginine and protein. Plant Physiol. 1986 Mar;80(3):760-5. PubMed PMID: 16664698; PubMed Central PMCID: PMC1075196. 17: Mitchell RE, Bieleski RL. Involvement of phaseolotoxin in halo blight of beans: transport and conversion to functional toxin. Plant Physiol. 1977 Nov;60(5):723-9. PubMed PMID: 16660172; PubMed Central PMCID: PMC542702. 18: Hernández-Flores JL, López-López K, Garcidueñas-Piña R, Jofre-Garfias AE, Alvarez-Morales A. The global arginine regulator ArgR controls expression of argF in Pseudomonas syringae pv. phaseolicola but is not required for the synthesis of phaseolotoxin or for the regulated expression of argK. J Bacteriol. 2004 Jun;186(11):3653-5. PubMed PMID: 15150254; PubMed Central PMCID: PMC415750. 19: Templeton MD, Sullivan PA, Shepherd MG. The inhibition of ornithine transcarbamoylase from Escherichia coli W by phaseolotoxin. Biochem J. 1984 Dec 1;224(2):379-88. PubMed PMID: 6393952; PubMed Central PMCID: PMC1144443. 20: Jahn O, Sauerstein J, Reuter G. Detection of two ornithine carbamoyltransferases in a phaseolotoxin-producing strain Pseudomonas syringae pv. phaseolicola. J Basic Microbiol. 1985;25(8):543-6. PubMed PMID: 4087158.

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