Diphenylalanine

The most common use of the word Diphenylalanine refers to two Phenylalanine molecules joined together by a Peptide bond.

Diphenylalanine
Names
IUPAC name
2-amino-3,3-diphenyl-propionic acid
Identifiers
149597-92-2 (L-isomer) YesY
149597-91-1 (D-isomer) N
ChemSpider 10608219 YesY
Jmol interactive 3D Image
Image
Properties
C15H15NO2
Molar mass 241.11 g/mol
Appearance Solid
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).
N verify (what is YesYN ?)
Infobox references

Diphenylalanine is an unnatural amino acid. It is 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]

A possible synthesis starts from 3,3-diphenyl-propionic acid which is stereoselective aminated to the diphenylalanine.[2]

References

  1. Leifeng Cheng, Christopher A. Goodwin, Michael F. Schully, Vijay V. Kakkar, and 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 and 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.


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