Enantiopure Peptide-Functionalized Metal–Organic Frameworks

We present herein the first example of metal–organic frameworks postfunctionalized with peptides. Our microwave-assisted postsynthetic modification method yields enantiopure peptides anchored inside MOF cavities. Al-MIL-101-NH2, In-MIL-68-NH2, and Zr-UiO-66-NH2 were chosen as starting platforms. A s...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-07, Vol.137 (29), p.9409-9416
Main Authors: Bonnefoy, Jonathan, Legrand, Alexandre, Quadrelli, Elsje Alessandra, Canivet, Jérôme, Farrusseng, David
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Catalysis
Chemical Sciences
Dipeptides - chemistry
Ketones - chemistry
Material chemistry
Microwaves
Models, Molecular
Molecular Conformation
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Stereoisomerism
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Summary:We present herein the first example of metal–organic frameworks postfunctionalized with peptides. Our microwave-assisted postsynthetic modification method yields enantiopure peptides anchored inside MOF cavities. Al-MIL-101-NH2, In-MIL-68-NH2, and Zr-UiO-66-NH2 were chosen as starting platforms. A single amino acid and various oligopeptides are grafted with yields up to 60% after a 30 min microwave-assisted coupling-deprotection sequence. This allows efficient preparation of a library of functional hybrid solids for molecular recognition applications such as sensing, separation, or asymmetric catalysis, as demonstrated here for the chiral aldol reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b05327