Diphenylalanine

Diphenylalanine

Diphenylalanine
Names
Preferred IUPAC name 2-Amino-3,3-diphenylpropanoic acid
Identifiers
CAS Number	(L-isomer): 149597-92-2  Y (D-isomer): 149597-91-1  Y
3D model (JSmol)	Interactive image
ChemSpider	(L-isomer): 143073  N
ECHA InfoCard	100.153.616
PubChem CID	(L-isomer): 162977 (D-isomer): 1520861
UNII	(L-isomer): L1ZWG54X8B (D-isomer): H2JAP020MP
CompTox Dashboard (EPA)	DTXSID80933685
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
SMILES OC(C(N)C(C2=CC=CC=C2)C1=CC=CC=C1)=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 the unnatural amino acid with the formula (C₆H₅)₂CHCH(NH₂)CO₂H. The compound is structurally related to the amino acids alanine and phenylalanine. It has been used for the synthesis of pseudopeptide analogues that 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.