MedKoo Cat#: 145438 | Name: Trifluoromethionine

Description:

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

Trifluoromethionine is a prodrug that is shown to be highly toxic in vitro to the anaerobic protozoan parasite Trichomonas vaginalis. Trifluoromethionine represents a lead compound for a novel class of anti-infective drugs with potential as chemotherapeutic agents against a range of prokaryotic and eukaryotic anaerobic pathogens.

Chemical Structure

Trifluoromethionine
Trifluoromethionine
CAS#764-52-3

Theoretical Analysis

MedKoo Cat#: 145438

Name: Trifluoromethionine

CAS#: 764-52-3

Chemical Formula: C5H8F3NO2S

Exact Mass: 203.0200

Molecular Weight: 203.18

Elemental Analysis: C, 29.56; H, 3.97; F, 28.05; N, 6.89; O, 15.75; S, 15.78

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
Trifluoromethionine;
IUPAC/Chemical Name
S-(trifluoromethyl)-L-homocysteine
InChi Key
YLJLTSVBCXYTQK-VKHMYHEASA-N
InChi Code
1S/C5H8F3NO2S/c6-5(7,8)12-2-1-3(9)4(10)11/h3H,1-2,9H2,(H,10,11)/t3-/m0/s1
SMILES Code
N[C@@H](CCSC(F)(F)F)C(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 203.18 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: Penuliar GM, Furukawa A, Sato D, Nozaki T. Mechanism of trifluoromethionine resistance in Entamoeba histolytica. J Antimicrob Chemother. 2011 Sep;66(9):2045-52. doi: 10.1093/jac/dkr238. Epub 2011 Jun 14. PMID: 21676903. 2: Penuliar GM, Furukawa A, Nakada-Tsukui K, Husain A, Sato D, Nozaki T. Transcriptional and functional analysis of trifluoromethionine resistance in Entamoeba histolytica. J Antimicrob Chemother. 2012 Feb;67(2):375-86. doi: 10.1093/jac/dkr484. Epub 2011 Nov 22. PMID: 22110087. 3: Coombs GH, Mottram JC. Trifluoromethionine, a prodrug designed against methionine gamma-lyase-containing pathogens, has efficacy in vitro and in vivo against Trichomonas vaginalis. Antimicrob Agents Chemother. 2001 Jun;45(6):1743-5. doi: 10.1128/AAC.45.6.1743-1745.2001. PMID: 11353620; PMCID: PMC90540. 4: Sato D, Kobayashi S, Yasui H, Shibata N, Toru T, Yamamoto M, Tokoro G, Ali V, Soga T, Takeuchi T, Suematsu M, Nozaki T. Cytotoxic effect of amide derivatives of trifluoromethionine against the enteric protozoan parasite Entamoeba histolytica. Int J Antimicrob Agents. 2010 Jan;35(1):56-61. doi: 10.1016/j.ijantimicag.2009.08.016. Epub 2009 Nov 12. Erratum in: Int J Antimicrob Agents. 2010 Apr;35(4):417. PMID: 19910163. 5: Alston TA, Bright HJ. Conversion of trifluoromethionine to a cross-linking agent by gamma-cystathionase. Biochem Pharmacol. 1983 Mar 1;32(5):947-50. doi: 10.1016/0006-2952(83)90608-1. PMID: 6838645. 6: Duewel H, Daub E, Robinson V, Honek JF. Incorporation of trifluoromethionine into a phage lysozyme: implications and a new marker for use in protein 19F NMR. Biochemistry. 1997 Mar 18;36(11):3404-16. doi: 10.1021/bi9617973. PMID: 9116020. 7: Sato D, Yamagata W, Harada S, Nozaki T. Kinetic characterization of methionine gamma-lyases from the enteric protozoan parasite Entamoeba histolytica against physiological substrates and trifluoromethionine, a promising lead compound against amoebiasis. FEBS J. 2008 Feb;275(3):548-60. doi: 10.1111/j.1742-4658.2007.06221.x. PMID: 18199285. 8: Duewel HS, Honek JF. CNBr/formic acid reactions of methionine- and trifluoromethionine-containing lambda lysozyme: probing chemical and positional reactivity and formylation side reactions by mass spectrometry. J Protein Chem. 1998 May;17(4):337-50. doi: 10.1023/a:1022555232364. PMID: 9619587. 9: Yoshimura M, Nakano Y, Koga T. L-Methionine-gamma-lyase, as a target to inhibit malodorous bacterial growth by trifluoromethionine. Biochem Biophys Res Commun. 2002 Apr 12;292(4):964-8. doi: 10.1006/bbrc.2002.6747. PMID: 11944909. 10: Duewel HS, Daub E, Robinson V, Honek JF. Elucidation of solvent exposure, side-chain reactivity, and steric demands of the trifluoromethionine residue in a recombinant protein. Biochemistry. 2001 Nov 6;40(44):13167-76. doi: 10.1021/bi011381b. PMID: 11683625. 11: Sato D, Nozaki T. Methionine gamma-lyase: the unique reaction mechanism, physiological roles, and therapeutic applications against infectious diseases and cancers. IUBMB Life. 2009 Nov;61(11):1019-28. doi: 10.1002/iub.255. PMID: 19859976. 12: Colombani F, Cherest H, de Robichon-Szulmajster H. Biochemical and regulatory effects of methionine analogues in Saccharomyces cerevisiae. J Bacteriol. 1975 May;122(2):375-84. doi: 10.1128/jb.122.2.375-384.1975. PMID: 1092648; PMCID: PMC246067. 13: Ali V, Nozaki T. Current therapeutics, their problems, and sulfur- containing-amino-acid metabolism as a novel target against infections by "amitochondriate" protozoan parasites. Clin Microbiol Rev. 2007 Jan;20(1):164-87. doi: 10.1128/CMR.00019-06. PMID: 17223627; PMCID: PMC1797636. 14: Gadais C, Devillers E, Gasparik V, Chelain E, Pytkowicz J, Brigaud T. Probing the Outstanding Local Hydrophobicity Increases in Peptide Sequences Induced by Incorporation of Trifluoromethylated Amino Acids. Chembiochem. 2018 May 18;19(10):1026-1030. doi: 10.1002/cbic.201800088. Epub 2018 Apr 23. PMID: 29513394. 15: Kikuchi Y, Ohara N, Ueda O, Hirai K, Shibata Y, Nakayama K, Fujimura S. Porphyromonas gingivalis mutant defective in a putative extracytoplasmic function sigma factor shows a mutator phenotype. Oral Microbiol Immunol. 2009 Oct;24(5):377-83. doi: 10.1111/j.1399-302X.2009.00526.x. PMID: 19702950. 16: Choih SJ, Ferro AJ, Shapiro SK. Function of S-adenosylmethionine in germinating yeast ascospores. J Bacteriol. 1977 Jul;131(1):63-8. doi: 10.1128/jb.131.1.63-68.1977. PMID: 326770; PMCID: PMC235391. 17: Tokoro M, Asai T, Kobayashi S, Takeuchi T, Nozaki T. Identification and characterization of two isoenzymes of methionine gamma-lyase from Entamoeba histolytica: a key enzyme of sulfur-amino acid degradation in an anaerobic parasitic protist that lacks forward and reverse trans-sulfuration pathways. J Biol Chem. 2003 Oct 24;278(43):42717-27. doi: 10.1074/jbc.M212414200. Epub 2003 Aug 14. PMID: 12920135. 18: Shiio I, Ozaki H. Feedback inhibition by methionine and S-adenosylmethionine, and desensitization of homoserine O-acetyltransferase in Brevibacterium flavum. J Biochem. 1981 May;89(5):1493-500. doi: 10.1093/oxfordjournals.jbchem.a133342. PMID: 7275950. 19: Terzani F, Belhattab S, Le Guern A, Guitot K, Monasson O, Zanato C, Chelain E, Leroy-Dudal J, Pytkowicz J. Synthesis and biological evaluation of selective Pepstatin based trifluoromethylated inhibitors of Cathepsin D. Eur J Med Chem. 2024 Mar 5;267:116178. doi: 10.1016/j.ejmech.2024.116178. Epub 2024 Jan 24. PMID: 38295686. 20: Ronda L, Bazhulina NP, Morozova EA, Revtovich SV, Chekhov VO, Nikulin AD, Demidkina TV, Mozzarelli A. Exploring methionine γ-lyase structure-function relationship via microspectrophotometry and X-ray crystallography. Biochim Biophys Acta. 2011 Jun;1814(6):834-42. doi: 10.1016/j.bbapap.2010.06.017. Epub 2010 Jul 1. PMID: 20601224.