Spinnler, Katrin and von Kruechten, Lara and Konieczny, Adam and Schindler, Lisa and Bernhardt, Guenther and Keller, Max (2020) An Alkyne-functionalized Arginine for Solid-Phase Synthesis Enabling "Bioorthogonal" Peptide Conjugation. ACS MEDICINAL CHEMISTRY LETTERS, 11 (3). pp. 334-339. ISSN 1948-5875,
Full text not available from this repository. (Request a copy)Abstract
Lately, amino-functionalized N-omega-carbamoylated arginines were introduced as arginine surrogates enabling peptide labeling. However, this approach is hardly compatible with peptides also containing lysine or cysteine. Here, we present the synthesis of an alkyne-functionalized, N-omega-carbamoylated arginine building block (7), which is compatible with Fmoc-strategy solid-phase peptide synthesis. The alkynylated arginine was incorporated into three biologically active linear hexapeptides and into a cyclic pentapeptide. Peptide conjugation to an azido-functionalized fluorescent dye via "click" chemistry was successfully demonstrated. In the case of a peptide also containing lysine besides the alkyne-functionalized arginine, this was feasible in a "bioorthogonal" manner.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | Y-1 RECEPTOR ANTAGONISTS; NEUROPEPTIDE-Y; CARBAMOYLATED ARGININE; DEPROTECTION; POTENT; ACIDS; Alkyne-functionalized arginine; carbamoylated arginine; peptidic receptor ligand; peptide conjugation; peptide labeling; click chemistry |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Mar 2021 08:24 |
| Last Modified: | 29 Mar 2021 08:24 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44943 |
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