2,4,5-Trifluoro-L-phenylalanine
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2,4,5-Trifluoro-L-phenylalanine

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Category
Fluorinated amino acids
Catalog number
BAT-006712
CAS number
749847-57-2
Molecular Formula
C9H8F3NO2
Molecular Weight
219.16
2,4,5-Trifluoro-L-phenylalanine
IUPAC Name
(2S)-2-amino-3-(2,4,5-trifluorophenyl)propanoic acid
Synonyms
H-Phe(2,4,5-F3)-OH
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.46 g/cm3
Melting Point
230-235 °C
Boiling Point
304.1°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H8F3NO2/c10-5-3-7(12)6(11)1-4(5)2-8(13)9(14)15/h1,3,8H,2,13H2,(H,14,15)/t8-/m0/s1
InChI Key
SWJFYJHCOWRRLR-QMMMGPOBSA-N
Canonical SMILES
C1=C(C(=CC(=C1F)F)F)CC(C(=O)O)N
1. Inheritance of 2,4-dichlorophenoxyacetic acid (2,4-D) resistance in Amaranthus palmeri
Chandrima Shyam, Dallas E Peterson, Amit J Jhala, Mithila Jugulam Sci Rep. 2022 Dec 17;12(1):21822. doi: 10.1038/s41598-022-25686-1.
In this study, the inheritance of 2,4-D resistance in a multiple herbicide-resistant Palmer amaranth (KCTR) was investigated. Direct and reciprocal crosses were performed using 2,4-D-resistant KCTR and susceptible KSS plants to generate F1 progenies. 2,4-D dose-response assays were conducted to evaluate the response of progenies from each F1 family along with KCTR and KSS plants in controlled environmental growth chambers. Additionally, 2,4-D-resistant male and female plants from each of the F1 families were used in pairwise crosses to generate pseudo-F2 families. Segregation (resistance or susceptibility) of progenies from the F2 families in response to a discriminatory rate of 2,4-D (i.e., 560 g ae ha-1) was evaluated. Dose-response analysis of F1 progenies derived from direct and reciprocal crosses suggested that the 2,4-D resistance in KCTR is a nuclear trait. Chi-square analyses of F2 segregation data implied that 2,4-D resistance in KCTR is controlled by multiple gene(s). Overall, our data suggest that the 2,4-D resistance in KCTR Palmer amaranth is a nuclear inherited trait controlled by multiple genes. Such resistance can spread both via pollen or seed-mediated gene flow. In future, efforts will be directed towards identifying genes mediating 2,4-D resistance in KCTR population.
2. Biotransformation of 2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine (TTBP-TAZ) can contribute to high levels of 2,4,6-tribromophenol (2,4,6-TBP) in humans
Guomao Zheng, Luma Melo, Rishika Chakraborty, James E Klaunig, Amina Salamova Environ Int. 2022 Jan;158:106943. doi: 10.1016/j.envint.2021.106943. Epub 2021 Oct 28.
2,4,6-Tribromophenol (2,4,6-TBP) is a brominated flame retardant that accumulates in human tissues and is a potential toxicant. Previous studies found 2,4,6-TBP levels in human tissues were significantly higher than those of brominated flame retardants measured in the same samples. In contrast, the levels of 2,4,6-TBP in the environment and foodstuff are not elevated, suggesting a low potential for direct intake through environmental exposure or diet. Here, we hypothesized that high levels of 2,4,6-TBP in human tissues are partially from the indirect exposure sources, such as biotransformation of highly brominated substances. We conducted in vitro assays utilizing human and rat liver microsomes to compare the biotransformation rates of four highly brominated flame retardants, which could potentially transform to 2,4,6-TBP, including decabromodiphenyl ethane (DBDPE), 2,4,6-tris-(2,4,6-tribromophenoxy)-1,3,5-triazine (TTBP-TAZ), 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), and tetrabromobisphenol A (TBBPA). Our results show that TTBP-TAZ rapidly metabolizes in both human and rat liver microsomes with a half-life of 1.1 and 2.2 h, respectively, suggesting that TTBP-TAZ is a potential precursor of 2,4,6-TBP. In contrast, 2,4,6-TBP was not formed as a result of biotransformation of TBBPA, BTBPE, and DBDPE in both human and rat liver microsomes. We applied suspect and target screening to explore the metabolic pathways of TTBP-TAZ and identified 2,4,6-TBP as a major metabolite of TTBP-TAZ accounting for 87% of all formed metabolites. These in vitro results were further tested by an in vivo experiment in which 2,4,6-TBP was detected in the rat blood and liver at concentrations of 270 ± 110 and 50 ± 14 μg/g lipid weight, respectively, after being exposed to 250 mg/kg body weight/day of TTBP-TAZ for a week. The hepatic mRNA expression demonstrated that TTBP-TAZ significantly activates the aryl hydrocarbon receptor (AhR) and promotes fatty degeneration (18 and 28-fold change compared to control, respectively) in rats.
3. 3-Phenyl-1H-1,2,4-triazol-5-amine-5-phenyl-1H-1,2,4-triazol-3-amine (1/1)
Anton V Dolzhenko, Geok Kheng Tan, Lip Lin Koh, Anna V Dolzhenko, Wai Keung Chui Acta Crystallogr Sect E Struct Rep Online. 2008 Dec 17;65(Pt 1):o126. doi: 10.1107/S1600536808042165.
In the title compound, C(8)H(8)N(4)·C(8)H(8)N(4), two tautomers, viz. 3-phenyl-1,2,4-triazol-5-amine and 5-phenyl-1,2,4-triazol-3-amine, are crystallized together in equal amounts. The 3-phenyl-1,2,4-triazol-5-amine mol-ecule is essentially planar; the phenyl ring makes a dihedral angle of 2.3 (2)° with the mean plane of the 1,2,4-triazole ring. In the 5-phenyl-1,2,4-triazol-3-amine tautomer, the mean planes of the phenyl and 1,2,4-triazole rings form a dihedral angle of 30.8 (2)°. The π-electron delocalization of the amino group with the 1,2,4-triazole nucleus in the 3-phenyl-1,2,4-triazol-5-amine mol-ecule is more extensive than that in the 5-phenyl-1,2,4-triazol-3-amine tautomer. The mol-ecules are linked into a two-dimensional network parallel to (100) by N-H⋯N hydrogen bonds.
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