Tabtoxin

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

MedKoo CAT#: 597977

CAS#: 40957-90-2

Description: Tabtoxin is a dipeptide containing tabtoxinine-beta-lactam with threonine.

Chemical Structure

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Tabtoxin
CAS# 40957-90-2
Instruction

Theoretical Analysis

MedKoo Cat#: 597977
Name: Tabtoxin
CAS#: 40957-90-2
Chemical Formula: C11H19N3O6
Exact Mass: 289.13
Molecular Weight: 289.280
Elemental Analysis: C, 45.67; H, 6.62; N, 14.53; O, 33.18

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: Tabtoxin;

IUPAC/Chemical Name: (2S,3R)-2-(2-aminobutanamido)-3-hydroxy-4-((S)-3-hydroxy-2-oxoazetidin-3-yl)butanoic acid

InChi Key: UECKJIVUCBNITH-WRWSIIAISA-N

InChi Code: InChI=1S/C11H19N3O6/c1-2-5(12)8(16)14-7(9(17)18)6(15)3-11(20)4-13-10(11)19/h5-7,15,20H,2-4,12H2,1H3,(H,13,19)(H,14,16)(H,17,18)/t5?,6-,7+,11+/m1/s1

SMILES Code: O[C@H](C[C@@]1(O)C(NC1)=O)[C@@H](C(O)=O)NC(C(N)CC)=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 289.28 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:

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1: Arai T, Arimura Y, Ishikura S, Kino K. L-amino acid ligase from Pseudomonas syringae producing tabtoxin can be used for enzymatic synthesis of various functional peptides. Appl Environ Microbiol. 2013 Aug;79(16):5023-9. doi: 10.1128/AEM.01003-13. Epub 2013 Jun 14. PubMed PMID: 23770908; PubMed Central PMCID: PMC3754701.

2: Lydon J, Patterson CD. Detection of tabtoxin-producing strains of Pseudomonas syringae by PCR. Lett Appl Microbiol. 2001 Mar;32(3):166-70. PubMed PMID: 11264746.

3: Barta TM, Kinscherf TG, Willis DK. Regulation of tabtoxin production by the lemA gene in Pseudomonas syringae. J Bacteriol. 1992 May;174(9):3021-9. PubMed PMID: 1314808; PubMed Central PMCID: PMC205957.

4: Kinscherf TG, Coleman RH, Barta TM, Willis DK. Cloning and expression of the tabtoxin biosynthetic region from Pseudomonas syringae. J Bacteriol. 1991 Jul;173(13):4124-32. PubMed PMID: 1648077; PubMed Central PMCID: PMC208062.

5: Harzallah D, Larous L. The synthesis of tabtoxin peptide bond in Pseudomonas syringae pv. tabaci. Biochem Soc Trans. 1998 Nov;26(4):S383. PubMed PMID: 10047897.

6: Engst K, Shaw PD. Identification of a lysA-like gene required for tabtoxin biosynthesis and pathogenicity in Pseudomonas syringae pv. tabaci strain PTBR2.024. Mol Plant Microbe Interact. 1992 Jul-Aug;5(4):322-9. PubMed PMID: 1515668.

7: Marek ET, Dickson RC. Cloning and characterization of Saccharomyces cerevisiae genes that confer L-methionine sulfoximine and tabtoxin resistance. J Bacteriol. 1987 Jun;169(6):2440-8. PubMed PMID: 2884208; PubMed Central PMCID: PMC212086.

8: Dehbi F, Harzallah D, Larous L. Effects of nutritional factors on production of tabtoxin, a phytotoxin, by Pseudomonas syringae pv. tabaci. Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2001;66(2a):241-7. PubMed PMID: 12425044.

9: Kinscherf TG, Willis DK. The biosynthetic gene cluster for the beta-lactam antibiotic tabtoxin in Pseudomonas syringae. J Antibiot (Tokyo). 2005 Dec;58(12):817-21. PubMed PMID: 16506699.

10: Liu L, Shaw PD. Characterization of dapB, a gene required by Pseudomonas syringae pv. tabaci BR2.024 for lysine and tabtoxinine-beta-lactam biosynthesis. J Bacteriol. 1997 Jan;179(2):507-13. PubMed PMID: 8990304; PubMed Central PMCID: PMC178722.

11: Liu J, Le Y, Ye B, Zhen Y, Zhu C, Shen J, Zhang R. Tabtoxin-resistant protein: overexpression, purification, and characterization. Protein Expr Purif. 2002 Apr;24(3):439-44. PubMed PMID: 11922760.

12: Anzai H, Yoneyama K, Yamaguchi I. The nucleotide sequence of tabtoxin resistance gene (ttr) of Pseudomonas syringae pv. tabaci. Nucleic Acids Res. 1990 Apr 11;18(7):1890. PubMed PMID: 2336364; PubMed Central PMCID: PMC330613.

13: Frantz TA, Peterson DM, Durbin RD. Sources of ammonium in oat leaves treated with tabtoxin or methionine sulfoximine. Plant Physiol. 1982 Feb;69(2):345-8. PubMed PMID: 16662206; PubMed Central PMCID: PMC426207.

14: Ding Y, Li S, Li X, Sun F, Liu J, Zhao N, Rao Z. Site-directed mutagenesis and preliminary x-ray crystallographic studies of the tabtoxin resistance protein. Protein Pept Lett. 2003 Jun;10(3):255-63. PubMed PMID: 12871145.

15: He H, Ding Y, Bartlam M, Sun F, Le Y, Qin X, Tang H, Zhang R, Joachimiak A, Liu J, Zhao N, Rao Z. Crystal structure of tabtoxin resistance protein complexed with acetyl coenzyme A reveals the mechanism for beta-lactam acetylation. J Mol Biol. 2003 Jan 31;325(5):1019-30. PubMed PMID: 12527305.

16: Barta TM, Kinscherf TG, Uchytil TF, Willis DK. DNA sequence and transcriptional analysis of the tblA gene required for tabtoxin biosynthesis by Pseudomonas syringae. Appl Environ Microbiol. 1993 Feb;59(2):458-66. PubMed PMID: 7679566; PubMed Central PMCID: PMC202127.

17: Duke SO, Dayan FE. Modes of action of microbially-produced phytotoxins. Toxins (Basel). 2011 Aug;3(8):1038-64. doi: 10.3390/toxins3081038. Epub 2011 Aug 22. Review. Erratum in: Toxins (Basel). 2012;4(10):955. PubMed PMID: 22069756; PubMed Central PMCID: PMC3202864.

18: Wencewicz TA, Walsh CT. Pseudomonas syringae self-protection from tabtoxinine-β-lactam by ligase TblF and acetylase Ttr. Biochemistry. 2012 Oct 2;51(39):7712-25. doi: 10.1021/bi3011384. Epub 2012 Sep 19. PubMed PMID: 22994681.

19: He H, Ding Y, Cao Z, Shao Y, Bartlam M, Tang H, Jiang F, Liu Y, Liu J, Zhao N, Rao Z. Crystallization and preliminary X-ray crystallographic analysis of native and selenomethionyl recombinant tabtoxin-resistance protein complexed with acetyl-coenzyme A. Acta Crystallogr D Biol Crystallogr. 2001 Nov;57(Pt 11):1729-31. Epub 2001 Oct 25. PubMed PMID: 11679759.

20: Thomas MD, Langston-Unkefer PJ, Uchytil TF, Durbin RD. Inhibition of Glutamine Synthetase from Pea by Tabtoxinine-beta-lactam. Plant Physiol. 1983 Apr;71(4):912-5. PubMed PMID: 16662928; PubMed Central PMCID: PMC1066143.