Diphenylalanine

Diphenylalanine
Names
	IUPAC name 2-amino-3,3-diphenyl-propionic acid
Identifiers
CAS Number	149597-92-2 (L-isomer) ; 149597-91-1 (D-isomer) ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	10608219 ;
ECHA InfoCard	100.153.616
	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) Key: SAUDSWFPPKSVMK-UHFFFAOYSA-N ; 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).
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	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]

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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[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 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.