Diphenylalanine

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]

Diphenylalanine
Names
IUPAC name
2-amino-3,3-diphenyl-propionic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.153.616
UNII
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 YN ?)
Infobox references

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

A historical use of the term "diphenylalanine" refers to the dipeptide of phenylalanine.

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 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.CS1 maint: multiple names: authors list (link)


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