Phenylalanine

Phenylalanine
Skeletal formula
Skeletal formula of L-phenylalanine

L-Phenylalanine at physiological pH
ball-and-stick model[1]
space-filling model[1]
Names
Pronunciation US: /ˌfɛnəlˈæləniːn/ (listenⓘ), UK: /ˌfiːnaɪl-/
IUPAC name
Phenylalanine
Systematic IUPAC name
(S)-2-Amino-3-phenylpropanoic acid
Identifiers
  • L: 63-91-2 checkY
  • D/L: 150-30-1 checkY
  • D: 673-06-3 checkY
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.517
IUPHAR/BPS
KEGG
UNII
CompTox Dashboard (EPA)
SMILES
  • L: c1ccc(cc1)C[C@@H](C(=O)O)N
  • L Zwitterion: [NH3+][C@@H](CC1=CC=CC=C1)C([O-])=O
Properties
C9H11NO2
Molar mass 165.19 g·mol−1
Acidity (pKa) 1.83 (carboxyl), 9.13 (amino)[2]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phenylalanine (symbol Phe or F) is an essential α-amino acid.

This essential amino acid is neutral and nonpolar. This is because of the inert and hydrophobic nature of the benzyl side chain.

The L-isomer is used to biochemically form proteins coded for by DNA.

Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), epinephrine (adrenaline), and the skin pigment melanin. It is encoded by the codons UUU and UUC.

References

  1. 1 2 Ihlefeldt, Franziska Stefanie; Pettersen, Fredrik Bjarte; von Bonin, Aidan; Zawadzka, Malgorzata; Görbitz, Prof. Carl Henrik (2014). "The Polymorphs of L-Phenylalanine". Angewandte Chemie International Edition. 53 (49): 13600–13604. doi:10.1002/anie.201406886. PMID 25336255.
  2. ↑ Dawson RM, et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
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