Phenylalanine

chemical compound

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

Phenylalanine
Names
Pronunciation US: /ˌfɛnəlˈælənn/, UK: /ˌfnl-/
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
KEGG
UNII
  • 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

1
2
0
 
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

change
  1. 1.0 1.1 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.