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Chemical Compound Review:

Tic-AA 1,2,3,4- tetrahydroisoquinoline-3...

Synonyms: H-D-TIC-OH, H-DL-TIC-OH, CHEMBL11912, SureCN43168, AGN-PC-0CPWBO, ...

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Disease relevance of Tic-AA

The replacement of Phe in both pY + 1 and pY + 3 by Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) was also not tolerated due to steric hindrance [1].

High impact information on Tic-AA

The substitution of Phe1 in FRCRCFa by 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid produces a potent inhibitor (IC50 = 2-4 microM) [2].
Discovery of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid diamides that increase CFTR mediated chloride transport [3].
The kinetics of the spontaneous formation of 2,5-dioxopiperazines from peptides containing the Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) residue in the 2-position of the sequence has been studied in DMSO and water solution [4].

Chemical compound and disease context of Tic-AA

Constrained phenylalanine analogues. Preferred conformation of the 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) residue [5].

References

Design and biological evaluation of linear and cyclic phosphopeptide ligands of the N-terminal SH2 domain of protein tyrosine phosphatase SHP-1. Imhof, D., Wieligmann, K., Hampel, K., Nothmann, D., Zoda, M.S., Schmidt-Arras, D., Zacharias, M., Böhmer, F.D., Reissmann, S. J. Med. Chem. (2005) [Pubmed]
Inhibition of the cardiac sarcolemma Na+/Ca2+ exchanger by conformationally constrained small cyclic peptides. Khananshvili, D., Mester, B., Saltoun, M., Wang, X., Shaulov, G., Baazov, D. Mol. Pharmacol. (1997) [Pubmed]
Discovery of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid diamides that increase CFTR mediated chloride transport. Hirth, B.H., Qiao, S., Cuff, L.M., Cochran, B.M., Pregel, M.J., Gregory, J.S., Sneddon, S.F., Kane, J.L. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
Acid catalysis in the formation of dioxopiperazines from peptides containing tetrahydroisoquinoline-3-carboxylic acid at position 2. Capasso, S., Sica, F., Mazzarella, L., Balboni, G., Guerrini, R., Salvadori, S. Int. J. Pept. Protein Res. (1995) [Pubmed]
Constrained phenylalanine analogues. Preferred conformation of the 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) residue. Valle, G., Kazmierski, W.M., Crisma, M., Bonora, G.M., Toniolo, C., Hruby, V.J. Int. J. Pept. Protein Res. (1992) [Pubmed]

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