My watch list

Diphenylalanine

Diphenylalanine

IUPAC name	2-amino-3,3-diphenyl-propionic acid
Identifiers
CAS number	L-isomer:[149597-92-2] D-isomer:[149597-91-1]
Properties
Molecular formula	C₁₅H₁₅NO₂
Molar mass	241.11 g/mol
Appearance	Solid
Melting point	Additional recommended knowledge Daily Visual Balance Check What is the Correct Way to Check Repeatability in Balances? Weighing the right way 235 °C
Related Compounds
Related amino acids	Alanine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 to inhibit certain enzymes.^[1]

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

References

^ 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.
^ 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.