H-Tyr(3-F)-OH | 3-Fluoro-L-tyrosine | Amino Acid Derivatives

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Quality Control of H-Tyr(3-F)-OH Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Citations Show More

PH domain-mediated autoinhibition and oncogenic activation of Akt

Bae, Hwan ; Viennet, Thibault ; Park, Eunyoung ; Chu, Nam ; Salguero, Antonieta ; Eck, Michael J , et al.

DOI: 10.7554/elife.80148 PubMed ID: 35968932 eLife,2022,11,e80148.

Abstract: Akt is a Ser/Thr protein kinase that plays a central role in metabolism and cancer. Regulation of Akt’s activity involves an autoinhibitory intramolecular interaction between its pleckstrin homology (PH) domain and its kinase domain that can be relieved by C-tail phosphorylation. PH domain mutant E17K Akt is a well-established oncogene. Previously, we reported that the conformation of autoinhibited Akt may be shifted by small molecule allosteric inhibitors limiting the mechanistic insights from existing X-ray structures that have relied on such compounds (Chu et al., 2020). Here, we discover unexpectedly that a single mutation R86A Akt exhibits intensified autoinhibitory features with enhanced PH domain-kinase domain affinity. Structural and biochemical analysis uncovers the importance of a key interaction network involving Arg86, Glu17, and Tyr18 that controls Akt conformation and activity. Our studies also shed light on the molecular basis for E17K Akt activation as an oncogenic driver.

Purchased from AmBeed: 7423-96-3

Development of a single culture E. coli expression system for the enzymatic synthesis of fluorinated tyrosine and its incorporation into proteins

Noelle M. Olson ; Jorden A. Johnson ; Kerstin E. Peterson ; Stephen C. Heinsch ; Andrew P. Marshall ; Michael J. Smanski , et al.

DOI: 10.1016/j.jfluchem.2022.110014 PubMed ID: 37197608 J. Fluorine Chem.,2022,261,110014.

Abstract: Current experiments that rely on biosynthetic metabolic protein labeling with 19F often require fluorinated amino acids, which in the case of 2- and 3-fluorotyrosine can be expensive. However, using these amino acids has provided valuable insight into protein dynamics, structure, and function. Here, we develop a new in-cell method for fluorinated tyrosine generation from readily available substituted phenols and subsequent metabolic labeling of proteins in a single bacterial expression culture. This approach uses a dual-gene plasmid encoding for a model protein BRD4(D1) and a tyrosine phenol lyase from Citrobacter freundii, which catalyzes the formation of tyrosine from phenol, pyruvate, and ammonium. Our system demonstrated both enzymatic fluorotyrosine production and expression of 19F-labeled proteins as analyzed by 19F NMR and LC-MS methods. Further optimization of our system should provide a cost-effective alternative to a variety of traditional protein-labeling strategies.

Keywords: Fluorine NMR ; Fluorotyrosine ; Metabolic labeling ; Bromodomain ; Tyrosine phenol lyase

Purchased from AmBeed: 7423-96-3

Product Details of H-Tyr(3-F)-OH

CAS No. :	7423-96-3
Formula :	C₉H₁₀FNO₃
M.W :	199.18
SMILES Code :	O=C(O)[C@@H](N)CC1=CC=C(O)C(F)=C1
Synonyms :	3-Fluoro-L-tyrosine
MDL No. :	MFCD00002607
InChI Key :	VIIAUOZUUGXERI-ZETCQYMHSA-N
Pubchem ID :	643330

Safety of H-Tyr(3-F)-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of H-Tyr(3-F)-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 7423-96-3 ]

[ 7423-96-3 ] Synthesis Path-Downstream 1~35

1
[ 56-45-1 ]
[ 367-12-4 ]
[ 7423-96-3 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1175 - 1179.

2
[ 35068-04-3 ]
[ 7423-96-3 ]

References: [1]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.

3
[ 35068-04-3 ]
[ 7423-96-3 ]
[ 78709-81-6 ]

References: [1]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.

4
[ 7423-96-3 ]
[ 113021-03-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 7051 - 7054.

5
[ 60-18-4 ]
[ 7423-96-3 ]

References: [1]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.
[2]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.
[3]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.

6
[ 7423-96-3 ]
[ 41840-28-2 ]
[ 125218-33-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 826 - 828.

7
[ 7423-96-3 ]
[ 82911-69-1 ]
(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 6851 - 6858.

8
[ 367-12-4 ]
[ 127-17-3 ]
[ 7423-96-3 ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 6851 - 6858.
[2]Biochemistry,2010,vol. 49,p. 1557 - 1559.
[3]Journal of the American Chemical Society,2011,vol. 133,p. 15942 - 15945.
[4]Journal of the American Chemical Society,2014,vol. 136,p. 7643 - 7654.

9
[ 7423-96-3 ]
(R)-3-Fluoro-β-tyrosine [ No CAS ]
(R)-5-Fluoro-3,4-dihydroxy-β-phenylalanine [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2000,vol. 39,p. 2754 - 2756.

10
Escherichia coli ribonucleotide reductase R₂ subunit [ No CAS ]
[ 7423-96-3 ]
Escherichia coli ribonucleotide reductase R₂ subunit (3-fluoro-L-tyrosine)356Y mutant [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 1569 - 1579.

11
[ 7423-96-3 ]
[ 182756-65-6 ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 6851 - 6858.

12
[ 7423-96-3 ]
(S)-4-{(S)-2-[(S)-2-((S)-2-Amino-4-carboxy-butyrylamino)-3-carboxy-propionylamino]-3-carbamoyl-propionylamino}-4-[(S)-1-[(1S,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-2-(3-fluoro-4-phosphonooxy-phenyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 6851 - 6858.

13
[ 3417-91-2 ]
[ 7423-96-3 ]

References: [1]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.
[2]Journal of Fluorine Chemistry,1987,vol. 37,p. 267 - 278.

14
[ 7423-96-3 ]
[ 125218-20-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 826 - 828.

15
[ 7423-96-3 ]
C₄₈H₇₃FN₁₂O₁₄ [ No CAS ]
C₄₉H₇₅FN₁₂O₁₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 644 - 646.

16
[ 367-12-4 ]
[ 113-24-6 ]
[ 7423-96-3 ]

References: [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 731 - 736.

17
[ 7423-96-3 ]
[ 3958-60-9 ]
[ 1215680-48-0 ]

References: [1]Biochemistry,2010,vol. 49,p. 1557 - 1559.

18
[ 24424-99-5 ]
[ 7423-96-3 ]
[ 125218-33-9 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 7643 - 7654.

19
[ 24424-99-5 ]
[ 7423-96-3 ]
[ 1609638-41-6 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 7643 - 7654.

20
[ 462-06-6 ]
[ 127-17-3 ]
[ 55660-73-6 ]
[ 7423-96-3 ]

References: [1]ACS Catalysis,2015,vol. 5,p. 7503 - 7506.

21
[ 372-20-3 ]
[ 127-17-3 ]
[ 7423-96-3 ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 926 - 935.

22
[ 7423-96-3 ]
3'-fluoro-[2-³H]-L-tyrosine [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2016,vol. 59,p. 4 - 8.

23
[ 7423-96-3 ]
C₁₈H₁₅FN₂O₂ [ No CAS ]
C₁₈H₁₄F₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With fungal non-ribosomal peptide synthetase HqlA; at 16℃; for 48h;Enzymatic reaction;	General procedure: E.coli BAP1 harboring the plasmid pXY01 were cultivated in a Erlenmeyer flasks containing 30 ml liquid LB medium (1percent tryptone, 1percent sodium chloride and 0.5percent yeast extract) supplemented with 50 mug/mul kanamycin sulfate and grown at 37 °C to an absorption at 600 nm OD of 0.6.1 Isopropyl thiogalactoside (IPTG) was added to a final concentration of 0.1 mM and the cells were cultivated for further 16 h at 16°C for induction. To achieve a higher biomass concentration, the culture was concentrated to 4.5 ml and transferred to a 50 ml falcon tube. 1 mg substrate each was fed into the concentrated culture and shaken at 16°C for another two days. The supernatant obtained by centrifugation was extracted twice with dichloromethane. For structure elucidation, 30 or 70 mg substrate each was fed into 150 ml concentrated culture under the same condition as described above.

References: [1]Tetrahedron Letters,2018,vol. 59,p. 3084 - 3087.

24
[ 7423-96-3 ]
methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluoro-4-hydroxyphenyl)propanoate [ No CAS ]

References: [1]Patent: US2018/215758,2018,A1 .
[2]Patent: WO2019/121406,2019,A1 .

25
[ 7423-96-3 ]
methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluoro-4-((3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)propanoate [ No CAS ]

References: [1]Patent: US2018/215758,2018,A1 .
[2]Patent: WO2019/121233,2019,A1 .
[3]Patent: WO2019/121406,2019,A1 .

26
[ 7423-96-3 ]
(S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluoro-4-((3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)propanoic acid [ No CAS ]

References: [1]Patent: US2018/215758,2018,A1 .
[2]Patent: WO2019/121233,2019,A1 .

27
[ 7423-96-3 ]
tert-butyl (S)-(3-(3-fluoro-4-((3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-((1-methylpiperidin-4-yl)amino)-1-oxopropan-2-yl)carbamate [ No CAS ]

References: [1]Patent: US2018/215758,2018,A1 .

28
[ 7423-96-3 ]
(S)-2-amino-3-(3-fluoro-4-((3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-N-(1-methylpiperidin-4-yl)propanamide [ No CAS ]

References: [1]Patent: US2018/215758,2018,A1 .

29
[ 67-56-1 ]
[ 7423-96-3 ]
methyl (S)-2-amino-3-(3-fluoro-4-hydroxyphenyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.55 g	With thionyl chloride; at 20℃;Cooling with ice;	Step A. Methyl (S)-2-amino-3-(3-fluoro-4-hydroxyphenyl)propanoate (Intermediate 1A-a) 3-Fluoro-L-tyrosine (6.0 g, 30.12 mmol) was suspended in methanol (120 mL) and the mixture was cooled in an ice bath. Thionyl chloride (11 mL, 150.6 mmol) was added dropwise. The mixture was allowed to warm to RT and then stirred overnight. The solvent was evaporated and the residue dissolved in water (50 mL). After basifying the mixture using saturated aqueous sodium hydrogen carbonate, the product was extracted into ethyl acetate (4*40 mL). The combined organic extracts were dried (Na2SO4) and evaporated to give the desired product as a beige solid (4.55 g). LCMS (Method 4): Rt=0.65 min, m/z 214.1 [M+H]+
4.55 g	With thionyl chloride; at 20℃;Cooling with ice;	3-Fluoro-F-tyrosine (6.0 g, 30.12 mmol) was suspended in methanol (120 mF) and the mixture was cooled in an ice bath. Thionyl chloride (11 mF, 150.6 mmol) was added dropwise. The mixture was allowed to warm to RT and then stirred overnight. The solvent was evaporated and the residue dissolved in water (50 mF). After basifying the mixture using saturated aqueous sodium hydrogen carbonate, the product was extracted four times with ethyl acetate. The combined organic extracts were dried (Na2S04) and evaporated to give the desired product as a beige solid (4.55 g). LCMS (Method 3): Rt = 0.65 min, m/z 214.1 [M+H]+
4.55 g	With thionyl chloride; at 20℃;Cooling with ice;	3-Fluoro-L-tyrosine (6.0 g, 30.12 mmol) was suspended in methanol (120 mL) and the mixture was cooled in an ice bath. Thionyl chloride (11 mL, 150.6 mmol) was added drop wise. The mixture was allowed to warm to RT and then stirred overnight. The solvent was evaporated and the residue dissolved in water (50 mL). After basifying the mixture using saturated aqueous sodium hydrogen carbonate, the product was extracted four times into ethyl acetate. The combined organic extracts were dried (Na2S04) and evaporated to give the desired product as a beige solid (4.55 g). (0497) LCMS (Method 3): Rt = 0.65 min, m/z 214.1 [M+H]+

References: [1]Patent: US2018/215758,2018,A1 .Location in patent: Paragraph 0440-0441.
[2]Patent: WO2019/121233,2019,A1 .Location in patent: Page/Page column 30; 31.
[3]Patent: WO2019/121406,2019,A1 .Location in patent: Page/Page column 60.

30
[ 7423-96-3 ]
tert-butyl (S)-(3-(3-fluoro-4-((3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H- pyrrolo[2,3-b]pyridin-4-yl)oxy)phenyl)-1-oxo-1-(2-(2-phenylacetyl)hydrazineyl)propan-2-yl)carbamate [ No CAS ]