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Nombre químico: (R)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid // Sinónimos: Fmoc-D-Tic-OH, (R)-Fmoc-1,2,3,4-tetrahydroisoquinoneline-1-carboxylic acid, 2-(9H-Fluoren-9-ylmethyl) (1R)-3,4-dihydro-1,2(1H)-isoquinolinedicarboxylate
from 450,00 €
1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid (TIQ) containing building blocks have gained ground in the design of peptide ligands, with improved selectivity towards a particular type of receptor: the side-chain topology of these amino acids is rather restricted relative to the peptide backbone, allowing less conformational variability. Additionally, TIQ can be used in the synthesis of promising matrix metalloproteinase (MMP) inhibitors and in gonadotropine-releasing hormone (GnRH) receptor antagonists.
Exploiting differences in caspase-2 and -3 S2 subsites for selectivity: Structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors; M. C. Maillard, F. A. Brookfield, S. M. Courtney, F. M. Eustache, M. J. Gemkow, R. K. Handel, L. C. Johnson, P. D. Johnson, M. A. Kerry, F. Krieger, M. Meniconi, I.Munoz-Sanjuán, J. J. Palfrey, H. Park, S. Schaertl, M. G. Taylor, D. Weddell, C. Dominguez; Bioorg. Med. Chem. 2011; 19(19): 5833-5851. https://doi.org/10.1016/j.bmc.2011.08.020
Caspase-2 Inhibitor Blocks Tau Truncation and Restores Excitatory Neurotransmission in Neurons Modeling FTDP-17 Tauopathy; G. Singh, P. Liu, K. R. Yao, J. M. Strasser, C. Hlynialuk, K. Leinonen-Wright, P. J. Teravskis, J. M. Choquette, J. Ikramuddin, M. Bresinsky, K. M. Nelson, D. Liao, K. H. Ashe, M. A. Walters, S. Pockes; ACS Chem. Neurosci. 2022; 13(10): 1549-1557. https://doi.org/10.1021/acschemneuro.2c00100
Molecular and Conformational Determinants of Pituitary Adenylate Cyclase-Activating Polypeptide (PACAP) for Activation of the PAC1 Receptor; S. Bourgault, D. Vaudry, I. Ségalas-Milazzo, L. Guilhaudis, A. Couvineau, M. Laburthe, H. Vaudry, A. Fournier; J. Med. Chem. 2009; 52(10): 3308-3316. https://doi.org/10.1021/jm900291j
Development and Pharmacological Characterization of Conformationally Constrained Urotensin II-Related Peptide Agonists; D. Chatenet, B. Folch, D. Feytens, M. Létourneau, D. Tourwé, N. Coucet, A. Fournier; J. Med. Chem. 2013; 56(23): 9612-9622. https://doi.org/10.1021/jm401153j
Discovery of a Parenteral Small Molecule Coagulation Factor XIa Inhibitor Clinical Candidate (BMS-962212); D. J. P. Pinot, M. J. Orwat, L. M. Smith, M. L. Quan, P. Y. S. Lam, K. A. Rossi, A. Apedo, J. M. Bozarth, Y. Wu, J. J. Zheng, B. Xin, N. Toussaint, P. Stetsko, O. Gudmundsson, B. Maxwell, E. J. Crain, P. C. Wong, Z. Lou, T. W. Harper, S. A. Chacko, J. E. Myers, S. Sheriff, H. Zhang, X. Hou, A. Mathur, D. A. Seiffert, R. R. Wexler, J. M. Luettgen, W. R. Ewing; J. Med. Chem. 2017; 60(23): 9703-9723. https://doi.org/10.1021/acs.jmedchem.7b01171
