Guest-adaptable and water-stable peptide-based porous materials by imidazolate side chain control

Katsoulidis, A. P. et al. (2014) Guest-adaptable and water-stable peptide-based porous materials by imidazolate side chain control. Angewandte Chemie (International Edition), 53(1), pp. 193-198. (doi: 10.1002/anie.201307074) (PMID:24302659) (PMCID:PMC3995008)

Abstract

The peptide-based porous 3D framework, ZnCar, has been synthesized from Zn2+ and the natural dipeptide carnosine (β-alanyl-L-histidine). Unlike previous extended peptide networks, the imidazole side chain of the histidine residue is deprotonated to afford Zn–imidazolate chains, with bonding similar to the zeolitic imidazolate framework (ZIF) family of porous materials. ZnCar exhibits permanent microporosity with a surface area of 448 m2 g−1, and its pores are 1D channels with 5 Å openings and a characteristic chiral shape. This compound is chemically stable in organic solvents and water. Single-crystal X-ray diffraction (XRD) showed that the ZnCar framework adapts to MeOH and H2O guests because of the torsional flexibility of the main His-β-Ala chain, while retaining the rigidity conferred by the Zn–imidazolate chains. The conformation adopted by carnosine is driven by the H bonds formed both to other dipeptides and to the guests, permitting the observed structural transformations.

• Item Type: Articles
• Additional Information: Funded by: Funded Access: EPSRC. Grant Numbers: EP/J008834, EP/H000925 EPSRC. Grant Number: EP/L000202
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Adams, Dave
• Authors: Katsoulidis, A. P., Park, K. S., Antypov, D., Martí-Gastaldo, C., Miller, G. J., Warren, J. E., Robertson, C. M., Blanc, F., Darling, G. R., Berry, N. G., Purton, J. A., Adams, D. J., and Rosseinsky, M. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Angewandte Chemie (International Edition)
• Publisher: Wiley - V C H Verlag GmbH & Co. KGaA
• ISSN: 1433-7851
• ISSN (Online): 1521-3773
• Published Online: 02 December 2013
• Copyright Holders: Copyright © 2014 The Authors
• First Published: First published in Angewandte Chemie International Edition 53(1): 193-198
• Publisher Policy: Reproduced under a Creative Commons license