Diphenylalanine
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IUPAC name
2-amino-3,3-diphenyl-propionic acid
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Identifiers | |
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3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.153.616 |
CompTox Dashboard (EPA)
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Properties | |
C15H15NO2 | |
Molar mass | 241.11 g/mol |
Appearance | Solid |
Melting point | 235 °C (455 °F; 508 K) |
Related compounds | |
Related amino acids
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Alanine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
A possible synthesis starts from 3,3-diphenyl-propionic acid which is stereoselective aminated to the diphenylalanine.[2]
The more common, historical use of the term "diphenylalanine" refers to the dipeptide of phenylalanine CAS # 2577-40-4.
References
- ^ 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.
- ^ 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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