3-Fluoro-L-phenylalanine (BAT-007836)
* For research use only

3-Fluoro-L-phenylalanine is a phenylalanine derivative that is L-phenylalanine in which the hydrogen at position 3 on the benzene ring is replaced by a fluoro group. It is a L-phenylalanine derivative, a non-proteinogenic L-alpha-amino acid and a member of monofluorobenzenes.

Category
Fluorinated amino acids
Catalog number
BAT-007836
CAS number
19883-77-3
Molecular Formula
C9H10FNO2
Molecular Weight
183.18
3-Fluoro-L-phenylalanine
Synonyms
L-Phe(3-F)-OH; m-Fluoro-L-phenylalanine; (S)-2-Amino-3-(3'-fluorophenyl)propanoic acid; L-3-fluorophenylalanine; 3-fluoro-l-phe; h-phe(3-f)-oh; (2S)-2-amino-3-(3-fluorophenyl)propanoic acid; L-Phenylalanine, 3-fluoro-; l-3-fluorophe; l-3-fluoro phenylalanine; l-(3-fluorophenyl)alanine; m-Fl-phenylalanine; h-m-fluoro-phe-oh
Appearance
White to off-white powder
Purity
≥ 98% (HPLC, Chiral HPLC,)
Density
1.293±0.06 g/cm3 (Predicted)
Melting Point
198.0-200.5 °C (dec.)
Boiling Point
305.0±32.0 °C (Predicted)
Storage
Store at RT
1.Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159.
Xu Y1, Zhan J, Wijeratne EM, Burns AM, Gunatilaka AA, Molnár I. J Nat Prod. 2007 Sep;70(9):1467-71. Epub 2007 Sep 6.
Precursor-directed biosynthesis was used to produce analogues of the cyclic depsipeptide mycotoxin beauvericin (1) using the filamentous fungus Beauveria bassiana ATCC 7159. Feeding 30 analogues of D-2-hydroxyisovalerate and L-phenylalanine, the natural 2-hydroxycarboxylic acid and amino acid precursors of beauvericin, led to the biosynthesis of novel beauvericins. Six of these were isolated and characterized, and their cytotoxicity and directional cell migration (haptotaxis) inhibitory activity against the metastatic prostate cancer cell line PC-3M were evaluated. Replacement of one, two, or all three of the D-2-hydroxyisovalerate constituents in beauvericin (1) with 2-hydroxybutyrate moieties (beauvericins G(1-3), compounds 2-4) caused a parallel decline of cell migration inhibitory activity and cytotoxicity, suggesting a requirement for a branched side chain for both of these biological activities at the corresponding positions of beauvericins.
Bio Calculators
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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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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