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
CAS Number	149597-92-2 (L-isomer)^Y 149597-91-1 (D-isomer)^N
ChemSpider	10608219^Y
Jmol interactive 3D	Image Image
InChI 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)^Y Key: SAUDSWFPPKSVMK-UHFFFAOYSA-N^Y InChI=1/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) Key: SAUDSWFPPKSVMK-UHFFFAOYAY
SMILES OC(C(N)C(C2=CC=CC=C2)C1=CC=CC=C1)=O CC(N(c1ccccc1)c2ccccc2)C(O)=O
Properties
Chemical formula	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

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

↑ 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.
↑ 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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