Product Focus: Arginine Derivatives

Arginine is characterized by its amphiphilic side chain, with a C3 alkyl chain terminated by a positively charged guanidino group. Since the latter can undergo hydrogen bonding as well as ionic interactions with binding partners, Arginine residues are frequently involved in cellular recognition processes. Consequently, derivatives of Arginine are highly sought after, be it for the introduction of Arg-mimetics to improve pharmacokinetic properties of therapeutic peptides, or to introduce an Arg derivative suitable for site-selective modification.

Selection of derivatives of Arginine accessible through our synthetic approach.

Our arginine platform allows us to design derivatives bearing substitutions on one guanidino nitrogen based on virtually any commercially available amine. A process is available to provide Fmoc- and Pbf-protected derivatives, which can instantly be used in any Fmoc/tBu solid phase peptide synthesis protocol.

➔ Do you require a different Arginine derivative? Do not hesitate to contact our Custom Synthesis Service.

References:

• Fluorescence Labeling of Neurotensin(8-13) via Arginine Residues Gives Molecular Tools with High Receptor Affinity; M. Keller, S. A. Mahuroof, V. Hong Yee, J. Carpenter, L. Schindler, T. Littmann, A. Pegoli, H. Hubner, G. Bernhardt, P. Gmeiner and N. D. Holliday; ACS Med Chem Lett 2020; 11: 16-22. https://doi.org/10.1021/acsmedchemlett.9b00462
• Mimicking of Arginine by Functionalized N(omega)-Carbamoylated Arginine As a New Broadly Applicable Approach to Labeled Bioactive Peptides: High Affinity Angiotensin, Neuropeptide Y, Neuropeptide FF, and Neurotensin Receptor Ligands As Examples; M. Keller, K. K. Kuhn, J. Einsiedel, H. Hubner, S. Biselli, C. Mollereau, D. Wifling, J. Svobodova, G. Bernhardt, C. Cabrele, P. M. Vanderheyden, P. Gmeiner and A. Buschauer; J Med Chem 2016; 59: 1925-45. https://doi.org/10.1021/acs.jmedchem.5b01495
• N(omega)-Carbamoylation of the Argininamide Moiety: An Avenue to Insurmountable NPY Y1 Receptor Antagonists and a Radiolabeled Selective High-Affinity Molecular Tool ([(3)H]UR-MK299) with Extended Residence Time; M. Keller, S. Weiss, C. Hutzler, K. K. Kuhn, C. Mollereau, S. Dukorn, L. Schindler, G. Bernhardt, B. Konig and A. Buschauer; J Med Chem 2015; 58: 8834-49. https://doi.org/10.1021/acs.jmedchem.5b00925