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 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]

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.