The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors

Janke D, Sommerhoff CP, Schaschke N (2011)
Bioorganic & Medicinal Chemistry 19(23): 7236-7243.

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Abstract
beta-Tryptase, a mast-cell specific serine protease with trypsin-like activity, has emerged in the last years as a promising novel therapeutic target in the field of allergic inflammation. Recently, we have developed a potent and selective beta-tryptase inhibitor based on the natural product cyclotheonamide E4 by implementing a basic P3 residue that addresses the determinants of the extended substrate specificity of beta-tryptase. To further improve the affinity/selectivity profile of this lead structure, we have now investigated beta-homo-3-aminomethylphenylalanine as S1 ligand. In contrast to the corresponding beta-homo amino acids derived from lysine or arginine, we demonstrate that this particular basic beta-homo amino acid is a privileged S1 ligand for the development of beta-tryptase inhibitors. Besides affinity, selectivity and reduced basicity, these novel cyclotheonamide E4 analogs show excellent stability in human plasma and serum. (C) 2011 Elsevier Ltd. All rights reserved.
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Janke D, Sommerhoff CP, Schaschke N. The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry. 2011;19(23):7236-7243.
Janke, D., Sommerhoff, C. P., & Schaschke, N. (2011). The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry, 19(23), 7236-7243.
Janke, D., Sommerhoff, C. P., and Schaschke, N. (2011). The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry 19, 7236-7243.
Janke, D., Sommerhoff, C.P., & Schaschke, N., 2011. The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry, 19(23), p 7236-7243.
D. Janke, C.P. Sommerhoff, and N. Schaschke, “The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors”, Bioorganic & Medicinal Chemistry, vol. 19, 2011, pp. 7236-7243.
Janke, D., Sommerhoff, C.P., Schaschke, N.: The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry. 19, 7236-7243 (2011).
Janke, Dennis, Sommerhoff, Christian P., and Schaschke, Norbert. “The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors”. Bioorganic & Medicinal Chemistry 19.23 (2011): 7236-7243.
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A new approach to inhibit human β-tryptase by protein surface binding of four-armed peptide ligands with two different sets of arms.
Jiang QQ, Bartsch L, Sicking W, Wich PR, Heider D, Hoffmann D, Schmuck C., Org. Biomol. Chem. 11(10), 2013
PMID: 23358683

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