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Chemical Compound Review:

SureCN180086 2-amino-3-phenyl-butanoic acid

Synonyms: AG-E-64662, NSC-518100, KB-19779, CTK8H6869, NSC518100, ...

Nogle, L.M. et al., Mosberg, H.I. et al., Misicka, A. et al., Smith, D.D. et al., Edmondson, S.D. et al., et al.

Xu, Wei, Mathvink, Edmondson, Mastracchio, Eiermann, He, Leone, Leiting, Lyons, Marsilio, Patel, Petrov, Wu, Thornberry, Weber, Smith, Saha, Fang, Schaffert, Waugh, Zeng, Toth, Hulce, Abel, Nogle, Mann, Watts, Zhang, Edmondson, Mastracchio, Duffy, Eiermann, He, Ita, Leiting, Leone, Lyons, Makarewicz, Patel, Petrov, Wu, Thornberry, Weber,

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Disease relevance of beta-Methylphenylalanine

The C-terminal Phe was replaced by Gly, cyclohexylalanine (Cha), Tyr, all four isomers of beta-methylphenylalanine (beta-MePhe), and l- and d-tetrahydroisoquinoline carboxylic acid (Tic), resulting in analogues 3-11 [1].

High impact information on beta-Methylphenylalanine

The in vitro pharmacological properties and conformational features of analogs of the delta opioid receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) in which the Phe3 residue was replaced by each of the four stereoisomers of beta-methylphenylalanine (beta-MePhe) were investigated [2].
anti-Substituted beta-methylphenylalanine derived amides have been shown to be potent DPP-IV inhibitors exhibiting excellent selectivity over both DPP8 and DPP9 [3].
anti-Substituted biaryl beta-methylphenylalanine derived amides have been shown to be potent DPP-IV inhibitors that suffer from suboptimal selectivity and pharmacokinetics [4].
Using the method of conformational constraint, we have designed and synthesized analogues of deltorphin I and dermenkephalin containing each of the four stereoisomers (2S,3S; 2S,3R; 2R,3S; 2R,3R) of the unusual amino acid beta-methylphenylalanine in position three [5].

Analytical, diagnostic and therapeutic context of beta-Methylphenylalanine

A direct preparative purification of all four isomers of the unnatural amino acid beta-methylphenylalanine was achieved using supercritical fluid chromatography (SFC) with stacked-injection [6].
Preparative separation and identification of derivatized beta-methylphenylalanine enantiomers by chiral SFC, HPLC and NMR for development of new peptide ligand mimetics in drug discovery [6].

References

Modifications to the N-terminus but not the C-terminus of calcitonin gene-related peptide(8-37) produce antagonists with increased affinity. Smith, D.D., Saha, S., Fang, G., Schaffert, C., Waugh, D.J., Zeng, W., Toth, G., Hulce, M., Abel, P.W. J. Med. Chem. (2003) [Pubmed]
Development of a model for the delta opioid receptor pharmacophore. 2. Conformationally restricted Phe3 replacements in the cyclic delta receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). Mosberg, H.I., Omnaas, J.R., Lomize, A., Heyl, D.L., Nordan, I., Mousigian, C., Davis, P., Porreca, F. J. Med. Chem. (1994) [Pubmed]
Discovery of potent, selective, and orally bioavailable pyridone-based dipeptidyl peptidase-4 inhibitors. Xu, J., Wei, L., Mathvink, R., Edmondson, S.D., Mastracchio, A., Eiermann, G.J., He, H., Leone, J.F., Leiting, B., Lyons, K.A., Marsilio, F., Patel, R.A., Petrov, A., Wu, J.K., Thornberry, N.A., Weber, A.E. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
Discovery of potent and selective orally bioavailable beta-substituted phenylalanine derived dipeptidyl peptidase IV inhibitors. Edmondson, S.D., Mastracchio, A., Duffy, J.L., Eiermann, G.J., He, H., Ita, I., Leiting, B., Leone, J.F., Lyons, K.A., Makarewicz, A.M., Patel, R.A., Petrov, A., Wu, J.K., Thornberry, N.A., Weber, A.E. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
Synthesis and biological properties of beta-MePhe3 analogues of deltorphin I and dermenkephalin: influence of biased chi 1 Phe3 residues on peptide recognition for delta-opioid receptors. Misicka, A., Cavagnero, S., Horvath, R., Davis, P., Porreca, F., Yamamura, H.I., Hruby, V.J. J. Pept. Res. (1997) [Pubmed]
Preparative separation and identification of derivatized beta-methylphenylalanine enantiomers by chiral SFC, HPLC and NMR for development of new peptide ligand mimetics in drug discovery. Nogle, L.M., Mann, C.W., Watts, W.L., Zhang, Y. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]

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