Welcome to Iris Biotech
For better service please confirm your country and language we detected.
confirm selection
For better service please confirm your country and language we detected.
Thank you very much for your interest in our products. All prices listed on our website are ex-works, Germany, and may attract customs duties when imported.
You may/will be contacted by the shipping company for additional documentation that may be required by the US Customs for clearance.
We offer you the convenience of buying through a local partner, Peptide Solutions LLC who can import the shipment as well as prepay the customs duties and brokerage on your behalf and provide the convenience of a domestic sale.
Continue to Iris Biotech GmbHSend request to US distributorPublished on 26.02.2025
In this blog, we present 1-carboxy-derivatives of 1,2,3,4-tetrahydroisoquinoline (TIQ) as novel proline analogs. They can act as helix breakers and may be used to fine-tune the secondary and tertiary structure of synthetic peptides. TIQs also have been successfully used in the design of specific inhibitors for the protease Cas-2, where TIQs modulate the affinity to the active center, in the synthesis of promising matrix metalloproteinase (MMP) inhibitors and for gonadotropin-releasing hormone (GnRH) receptor antagonists.
Overview of available Fmoc-protected TIQs as novel proline analogs: The 1-carboxy 1,2,3,4-tetrahydroisoquinolines are provided enantomerically pure; the methyl-substituted ones as racemates.
These Fmoc-protected building blocks can be directly used in Fmoc solid-phase peptide synthesis. Especially, the differently methyl-substituted derivatives are perfect for screening, e.g., to fine-tune the structure-activity relationship of your inhibitory molecule or ligand.
Schematic depiction of the steric consequences using the (S) and (R) varieties of our TIQs: The axial or equatorial orientation of the carboxy group affects the structure of the peptide chain, analog to proline.
Furthermore, we are also offering Fmoc- and Boc-protected as well as unprotected 3-carboxy 1,2,3,4-tetrahydroisoquinolines (TIC derivatives) and -hydroxyisoquinolines with similar properties. For structure details, please scroll-down to the related products at the bottom of this blog!
References:
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