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Chemical Compound Review:

AC1NWBO0 (Z)-2-amino-3-phenyl-prop-2- enoic acid

Synonyms: AG-G-75724, SureCN1081471, FT-0665646, DB04584, 7060-39-1, ...

Siddiqui, M.Z., Ciajolo, M.R. et al., Shimohigashi, Y. et al., Makowski, M. et al., Uma, K. et al., et al.

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High impact information on Phenyldehydroalanine

Dehydrophenylalanine (delta Phe) was incorporated into an antibiotic peptide gramicidin S (GS) in place of D-Phe4,4' to prepare an unsaturated analog [1].
Synthesis of tetrapeptide p-nitrophenylanilides containing dehydroalanine and dehydrophenylalanine and their influence on cathepsin C activity [2].
Few dehydrophenylalanine (deltaPhe) analogues (X-deltaPhe-Phe-Gly-X1, X = Ac-; Boc-; Z-; X1 = OMe; OH; ONH2) of virus replication inhibiting peptide (Z-D-Phe-Phe-Gly) were synthesized, and their solution conformations were investigated by 1H NMR, UV and circular dichroism (CD) spectroscopy [3].
The crystal and molecular structure of the pentapeptide Boc-D-Ala-delta Phe-Gly-delta Phe-D-Ala-OMe, containing two dehydrophenylalanine residues, was determined by x-ray diffraction [4].
Conformations of dehydrophenylalanine containing peptides. Nuclear Overhauser effect study of two acyclic tetrapeptides [5].

Gene context of Phenyldehydroalanine

Synthesis and conformational study of a cyclic hexapeptide analog of somatostatin containing dehydrophenylalanine [6].

References

[4,4'-(Z)-dehydrophenylalanine]gramicidin S with stabilized bioactive conformation and strong antimicrobial activity. Shimohigashi, Y., Kodama, H., Imazu, S., Horimoto, H., Sakaguchi, K., Waki, M., Uchida, H., Kondo, M., Kato, T., Izumiya, N. FEBS Lett. (1987) [Pubmed]
Synthesis of tetrapeptide p-nitrophenylanilides containing dehydroalanine and dehydrophenylalanine and their influence on cathepsin C activity. Makowski, M., Pawelczak, M., Latajka, R., Nowak, K., Kafarski, P. J. Pept. Sci. (2001) [Pubmed]
Dehydrophenylalanine analogues: conformational characterization. Siddiqui, M.Z. Int. J. Biol. Macromol. (1999) [Pubmed]
Crystal and molecular structure of Boc-D-Ala-delta Phe-Gly-delta Phe- D-Ala-OMe: a 3 10-helical dehydropeptide. Ciajolo, M.R., Tuzi, A., Pratesi, C.R., Fissi, A., Pieroni, O. Biopolymers (1990) [Pubmed]
Conformations of dehydrophenylalanine containing peptides. Nuclear Overhauser effect study of two acyclic tetrapeptides. Uma, K., Chauhan, V.S., Kumar, A., Balaram, P. Int. J. Pept. Protein Res. (1988) [Pubmed]
Synthesis and conformational study of a cyclic hexapeptide analog of somatostatin containing dehydrophenylalanine. Brady, S.F., Cochran, D.W., Nutt, R.F., Holly, F.W., Bennett, C.D., Paleveda, W.J., Curley, P.E., Arison, B.H., Saperstein, R., Veber, D.F. Int. J. Pept. Protein Res. (1984) [Pubmed]

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