3-Trifluoromethyl-L-phenylalanine (BAT-007843)

Category
Fluorinated amino acids
Catalog number
BAT-007843
CAS number
14464-68-7
Molecular Formula
C10H10F3NO2
Molecular Weight
233.19
3-Trifluoromethyl-L-phenylalanine
Alternative CAS
122839-48-9
Synonyms
L-Phe(3-CF3)-OH; H-L-Phe(3-trifluoromethyl)-OH; (S)-2-Amino-3-(3-trifluoromethyl-phenyl)propionic acid; 3-Trifluoromethyl-L-Phenylalanine; L-3-Trifluoromethylphenylalanine; (2S)-2-amino-3-[3-(trifluoromethyl)phenyl]propanoic acid; Phenylalanine, 3-(trifluoromethyl)-; D-3-Trifluoromethyphenylalanine; 3-(Trifluoromethyl)phenylalanine
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.364±0.06 g/cm3 (Predicted)
Melting Point
191-193 °C
Boiling Point
301.2±42.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H10F3NO2/c11-10(12,13)7-3-1-2-6(4-7)5-8(14)9(15)16/h1-4,8H,5,14H2,(H,15,16)/t8-/m0/s1
InChI Key
BURBNIPKSRJAIQ-QMMMGPOBSA-N
Canonical SMILES
C1=CC(=CC(=C1)C(F)(F)F)CC(C(=O)O)N
1.4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a potent inhibitor of bacterial phosphopantetheinyl transferase that attenuates secondary metabolism and thwarts bacterial growth.
Foley TL1, Rai G, Yasgar A, Daniel T, Baker HL, Attene-Ramos M, Kosa NM, Leister W, Burkart MD, Jadhav A, Simeonov A, Maloney DJ. J Med Chem. 2014 Feb 13;57(3):1063-78. doi: 10.1021/jm401752p. Epub 2014 Jan 22.
4'-Phosphopantetheinyl transferases (PPTases) catalyze a post-translational modification essential to bacterial cell viability and virulence. We present the discovery and medicinal chemistry optimization of 2-pyridinyl-N-(4-aryl)piperazine-1-carbothioamides, which exhibit submicromolar inhibition of bacterial Sfp-PPTase with no activity toward the human orthologue. Moreover, compounds within this class possess antibacterial activity in the absence of a rapid cytotoxic response in human cells. An advanced analogue of this series, ML267 (55), was found to attenuate production of an Sfp-PPTase-dependent metabolite when applied to Bacillus subtilis at sublethal doses. Additional testing revealed antibacterial activity against methicillin-resistant Staphylococcus aureus , and chemical genetic studies implicated efflux as a mechanism for resistance in Escherichia coli . Additionally, we highlight the in vitro absorption, distribution, metabolism, and excretion and in vivo pharmacokinetic profiles of compound 55 to further demonstrate the potential utility of this small-molecule inhibitor.
2.Effects of lorazepam and WAY-200070 in larval zebrafish light/dark choice test.
Chen F1, Chen S1, Liu S1, Zhang C1, Peng G2. Neuropharmacology. 2015 Aug;95:226-33. doi: 10.1016/j.neuropharm.2015.03.022. Epub 2015 Apr 1.
Zebrafish larvae spend more time in brightly illuminated area when placed in a light/dark testing environment. Here we report that the anxiolytic drugs lorazepam and diazepam increased the time larval fish spent in the dark compartment in the light/dark test. Lorazepam did not affect the visual induced optokinetic response of larval fish. Gene expression levels of c-fos and crh were significantly increased in the hypothalamus of fish larvae underwent light/dark choice behavior, whilst lorazepam treatment alleviated the increased c-fos and crh expressions. Furthermore, we found estrogen receptor β gene expression level was increased in fish larvae underwent light/dark choice. We next examined effects of estrogen receptor modulators (estradiol, BPA, PHTPP, and WAY-200070) in the light/dark test. We identified WAY-200070, a highly selective ERβ agonist significantly altered the light/dark choice behavior of zebrafish larvae. Further investigation showed WAY-200070 treatment caused a reduction of crh expression level in the hypothalamus, suggesting activation of ERβ signaling attenuate the stress response.
3.Structures and Energetics of Protonated Clusters of Methylamine with Phenylalanine Analogs, Characterized by Infrared Multiple Photon Dissociation Spectroscopy and Electronic Structure Calculations.
Kleisath E1, Marta RA1, Martens S1, Martens J1, McMahon T1. J Phys Chem A. 2015 Jun 25;119(25):6689-702. doi: 10.1021/acs.jpca.5b02794. Epub 2015 Jun 15.
Gas-phase clusters of protonated methylamine and phenylalanine (Phe) derivatives have been studied using infrared multiple photon dissociation (IRMPD) spectroscopy in combination with electronic structure calculations at the MP2/aug-cc-pVTZ//B3LYP/6-311+G(d,p) level of theory. Experiments were performed on several Phe derivatives including 4-chloro-l-phenylalanine (4Chloro-Phe), 4-nitro-l-phenylalanine (4Nitro-Phe), 3-cyano-l-phenylalanine (3Cyano-Phe), and 3-trifluoromethyl-l-phenylalanine (3CF3-Phe). Through comparisons between experimental IRMPD spectra and stimulated spectra obtained by electronic structure calculations, charge-solvated structures were found to be prevalent in both 4Chloro-Phe and 4Nitro-Phe, whereas 3Cyano-Phe favored zwitterionic structures and 3-CF3-Phe likely have both zwitterionic and charge-solvated structures present.
4.Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling.
Wang L1, Murai Y, Yoshida T, Ishida A, Masuda K, Sakihama Y, Hashidoko Y, Hatanaka Y, Hashimoto M. Org Lett. 2015 Feb 6;17(3):616-9. doi: 10.1021/ol503630z. Epub 2015 Jan 14.
Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2(-) is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
Bio Calculators
Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
g
Quick Inquiry
Verification code
Inquiry Basket