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MedKoo Cat#: 585281 | Name: Tentoxin

Description:

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

Tentoxin is a cyclic peptide from fungus Alternaria tenuis Auct. that inhibits F(1)-ATPase.

Chemical Structure

Tentoxin
Tentoxin
CAS#28540-82-1

Theoretical Analysis

MedKoo Cat#: 585281

Name: Tentoxin

CAS#: 28540-82-1

Chemical Formula: C22H30N4O4

Exact Mass: 414.2267

Molecular Weight: 414.51

Elemental Analysis: C, 63.75; H, 7.30; N, 13.52; O, 15.44

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
Tentoxin
IUPAC/Chemical Name
(3S,6S,12Z)-12-benzylidene-1,6,7-trimethyl-3-(2-methylpropyl)-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
InChi Key
SIIRBDOFKDACOK-LFXZBHHUSA-N
InChi Code
InChI=1S/C22H30N4O4/c1-14(2)11-17-22(30)26(5)18(12-16-9-7-6-8-10-16)21(29)23-13-19(27)25(4)15(3)20(28)24-17/h6-10,12,14-15,17H,11,13H2,1-5H3,(H,23,29)(H,24,28)/b18-12-/t15-,17-/m0/s1
SMILES Code
O=C([C@H](CC(C)C)NC([C@H](C)N(C)C(CNC/1=O)=O)=O)N(C)C1=C/C2=CC=CC=C2
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 414.51 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: Tucker WC, Du Z, Hein R, Richter ML, Gromet-Elhanan Z. Hybrid Rhodospirillum rubrum F(0)F(1) ATP synthases containing spinach chloroplast F(1) beta or alpha and beta subunits reveal the essential role of the alpha subunit in ATP synthesis and tentoxin sensitivity. J Biol Chem. 2000 Jan 14;275(2):906-12. PubMed PMID: 10625626. 2: Santolini J, Minoletti C, Gomis JM, Sigalat C, André F, Haraux F. An insight into the mechanism of inhibition and reactivation of the F(1)-ATPases by tentoxin. Biochemistry. 2002 May 14;41(19):6008-18. PubMed PMID: 11993995. 3: Marin S, Ramos AJ, Cano-Sancho G, Sanchis V. Mycotoxins: occurrence, toxicology, and exposure assessment. Food Chem Toxicol. 2013 Oct;60:218-37. doi: 10.1016/j.fct.2013.07.047. Epub 2013 Jul 29. Review. PubMed PMID: 23907020. 4: Steele JA, Uchytil TF, Durbin RD, Bhatnagar P, Rich DH. Chloroplast coupling factor 1: A species-specific receptor for tentoxin. Proc Natl Acad Sci U S A. 1976 Jul;73(7):2245-8. PubMed PMID: 16592333; PubMed Central PMCID: PMC430514. 5: Pinet E, Cavelier F, Verducci J, Girault G, Dubart L, Haraux F, Sigalat C, André F. Synthesis, structure, and properties of MeSer1-tentoxin, a new cyclic tetrapeptide which interacts specifically with chloroplast F1 H(+)-ATPase differentiation of inhibitory and stimulating effects. Biochemistry. 1996 Oct 1;35(39):12804-11. PubMed PMID: 8841123. 6: Tucker WC, Du Z, Hein R, Gromet-Elhanan Z, Richter ML. Role of the ATP synthase alpha-subunit in conferring sensitivity to tentoxin. Biochemistry. 2001 Jun 26;40(25):7542-8. PubMed PMID: 11412108. 7: Hu N, Mills DA, Huchzermeyer B, Richter ML. Inhibition by tentoxin of cooperativity among nucleotide binding sites on chloroplast coupling factor 1. J Biol Chem. 1993 Apr 25;268(12):8536-40. PubMed PMID: 8473298. 8: Delaforge M, Andre F, Jaouen M, Dolgos H, Benech H, Gomis JM, Noel JP, Cavelier F, Verducci J, Aubagnac JL, Liebermann B. Metabolism of tentoxin by hepatic cytochrome P-450 3A isozymes. Eur J Biochem. 1997 Nov 15;250(1):150-7. PubMed PMID: 9432003. 9: Jiménez JC, Chavarría B, López-Macià A, Royo M, Giralt E, Albericio F. Tentoxin as a scaffold for drug discovery. Total solid-phase synthesis of tentoxin and a library of analogues. Org Lett. 2003 Jun 12;5(12):2115-8. PubMed PMID: 12790542. 10: Reimer S, Selman BR. Tentoxin-induced binding of adenine nucleotides to soluble spinach chloroplast coupling factor 1. Biochim Biophys Acta. 1979 Mar 15;545(3):415-23. PubMed PMID: 154928. 11: Groth G, Hisabori T, Lill H, Bald D. Substitution of a single amino acid switches the tentoxin-resistant thermophilic F1-ATPase into a tentoxin-sensitive enzyme. J Biol Chem. 2002 Jun 7;277(23):20117-9. Epub 2002 Apr 9. PubMed PMID: 11943766. 12: Schnick C, Körtgen N, Groth G. Complete inhibition of the tentoxin-resistant F1-ATPase from Escherichia coli by the phytopathogenic inhibitor tentoxin after substitution of critical residues in the alpha - and beta -subunit. J Biol Chem. 2002 Dec 27;277(52):51003-7. Epub 2002 Oct 23. PubMed PMID: 12399471. 13: Ramm K, Ramm M, Liebermann B, Reuter G. Studies of the biosynthesis of tentoxin by Alternaria alternata. Microbiology. 1994 Dec;140 ( Pt 12):3257-66. PubMed PMID: 7881545. 14: Steele JA, Uchytil TF, Durbin RD, Bhatnagar PK, Rich DH. The stimulation of coupling factor 1 ATPase by tentoxin and its analogs. Biochem Biophys Res Commun. 1978 Sep 14;84(1):215-8. PubMed PMID: 153140. 15: Santolini J, Haraux F, Sigalat C, Moal G, André F. Kinetic analysis of tentoxin binding to chloroplast F1-ATPase. A model for the overactivation process. J Biol Chem. 1999 Jan 8;274(2):849-58. PubMed PMID: 9873024. 16: Groth G. Structure of spinach chloroplast F1-ATPase complexed with the phytopathogenic inhibitor tentoxin. Proc Natl Acad Sci U S A. 2002 Mar 19;99(6):3464-8. PubMed PMID: 11904410; PubMed Central PMCID: PMC122546. 17: Pavlova P, Shimabukuro K, Hisabori T, Groth G, Lill H, Bald D. Complete inhibition and partial Re-activation of single F1-ATPase molecules by tentoxin: new properties of the re-activated enzyme. J Biol Chem. 2004 Mar 12;279(11):9685-8. Epub 2004 Jan 22. PubMed PMID: 14739290. 18: Meyer WL, Templeton GE, Grable CI, Jones R, Kuyper LF, Lewis RB, Sigel CW, Woodhead SH. Use of 1-H nuclear magnetic resonance spectroscopy for sequence and configuration analysis of cyclic tetrapeptides. The structure of Tentoxin-1,2a--d. J Am Chem Soc. 1975 Jun 25;97(13):3202-9. PubMed PMID: 1141586. 19: Minoletti C, Santolini J, Haraux F, Pothier J, André F. Rebuilt 3D structure of the chloroplast f1 ATPase-tentoxin complex. Proteins. 2002 Nov 15;49(3):302-20. PubMed PMID: 12360520. 20: Santolini J, Haraux F, Sigalat C, Munier L, André F. Interrelation between high and low affinity tentoxin binding sites in chloroplast F1-ATPase revealed by synthetic analogues. J Biol Chem. 1998 Feb 6;273(6):3343-50. PubMed PMID: 9452452.