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http://hdl.handle.net/10397/106056
Title: | Versatile synthesis of multivalent porphyrin–peptide conjugates by direct porphyrin construction on resin | Authors: | Wu, Y Chau, HF Yeung, YH Thor, W Kai, HY Chan, WL Wong, KL |
Issue Date: | 22-Aug-2022 | Source: | Angewandte chemie international edition, 22 Aug. 2022, v. 61, no. 34, e202207532 | Abstract: | Multifunctional porphyrin–peptide conjugates with different propensities for self-assembly into various supramolecular nanoarchitectures play important roles in advanced materials and biomedical research. However, preparing prefunctionalized core porphyrins by traditional low-yielding statistical synthesis and purifying them after peptide ligation through many rounds of HPLC purification is tedious and unsustainable. Herein, we report a novel integrated solid-phase synthetic protocol for the construction of porphyrin moieties from simple aldehydes and dipyrromethanes on resin-bound peptides directly to form mono-, cis/trans-di-, and trivalent porphyrin–peptide conjugates in a highly efficient and controllable manner; moreover, only single final-stage HPLC purification of the products is needed. This efficient strategy enables the rapid, greener, and substrate-controlled diversity-oriented synthesis of multivalent porphyrin–(long) peptide conjugate libraries for multifarious biological and materials applications. | Keywords: | Fluorescent peptides Multivalent porphyrin–peptide conjugates Porphyrins Solid-phase peptide synthesis Targeted bioimaging |
Publisher: | Wiley-VCH | Journal: | Angewandte chemie international edition | ISSN: | 1433-7851 | EISSN: | 1521-3773 | DOI: | 10.1002/anie.202207532 | Rights: | © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License (https://creativecommons.org/licenses/by-nc-nd/4.0/), which permits use and distributionin any med-ium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. The following publication YWu, Y., Chau, H. F., Yeung, Y. H., Thor, W., Kai, H. Y., Chan, W. L., & Wong, K. L. (2022). Versatile Synthesis of Multivalent Porphyrin–Peptide Conjugates by Direct Porphyrin Construction on Resin. Angewandte Chemie International Edition, 61(34), e202207532 is available at https://doi.org/10.1002/anie.202207532. |
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