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3-Fluoro-L-phenylalanine

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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

Specification
Reference Reading

IUPAC Name

(2S)-2-amino-3-(3-fluorophenyl)propanoic acid

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

InChI

InChI=1S/C9H10FNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1

InChI Key

VWHRYODZTDMVSS-QMMMGPOBSA-N

Canonical SMILES

C1=CC(=CC(=C1)F)CC(C(=O)O)N

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.