Diphenylalanine

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Diphenylalanine
Diphenylalanine Diphenylalanine structure.svg
Diphenylalanine
Names
Preferred IUPAC name
2-Amino-3,3-diphenylpropanoic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.153.616 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C15H15NO2/c1-12(15(17)18)16(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-12H,1H3,(H,17,18) Yes check.svgY
    Key: SAUDSWFPPKSVMK-UHFFFAOYSA-N Yes check.svgY
  • OC(C(N)C(C2=CC=CC=C2)C1=CC=CC=C1)=O
Properties
C15H15NO2
Molar mass 241.11 g/mol
AppearanceSolid
Melting point 235 °C (455 °F; 508 K)
Related compounds
Related amino acids
Alanine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diphenylalanine is a term that has recently been used to describe the unnatural amino acid similar to the two amino acids alanine and phenylalanine. It has been used for the synthesis of pseudopeptide analogues which are capable of inhibiting certain enzymes. [1]

Individual enantiomers of this compound can be synthesized via electrophilic amination of a chiral oxazolidinone derivative of 3,3-diphenylpropanoic acid. [2]

A historical use of the term diphenylalanine refers to the dipeptide of phenylalanine (Phe-Phe  [ Wikidata ]).

References

  1. Leifeng Cheng; Christopher A. Goodwin; Michael F. Schully; Vijay V. Kakkar; Goran Claeson (1992). "Synthesis and biological activity of ketomethylene pseudopeptide analogs as thrombin inhibitors". Journal of Medicinal Chemistry . 35 (18): 3364–3369. doi:10.1021/jm00096a010. PMID   1527787.
  2. Huai G. Chen; V. G. Beylin; M. Marlatt; B. Leja; O. P. Goel (1992). "Chiral cynthesis of D- and L-3,3-diphenylalanine (Dip), unusual α-amino acids for peptides of biological interest". Tetrahedron Letters . 33 (23): 3293–3296. doi:10.1016/S0040-4039(00)92070-7.