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Angew Chem Int Ed Engl. 2014 Jan 3;53(1):193-8. doi: 10.1002/anie.201307074. Epub 2013 Dec 2.

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

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1
Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD (UK).

Abstract

The peptide-based porous 3D framework, ZnCar, has been synthesized from Zn(2+) 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 m(2)  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 H2 O 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.

KEYWORDS:

imidazolates; metal-organic frameworks; microporous materials; peptides; structural adaptability

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