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Title

Dynamic Covalent Identification of an Efficient Heparin Ligand

AuthorsCorredor, Miriam ; Carbajo López, Daniel; Domingo, Cecilia; Pérez, Yolanda ; Bujons, Jordi; Messeguer, Àngel; Alfonso, Ignacio
KeywordsDynamics
Dynamic covalent chemistry
Glycosaminoglycans
Heparin
Molecular recognition
Supramolecular chemistry
Issue Date10-Sep-2018
PublisherWiley-Blackwell
CitationAngewandte Chemie - International Edition 57 (37): 11973-11977 (2018)
AbstractDespite heparin being the most widely used macromolecular drug, the design of small-molecule ligands to modulate its effects has been hampered by the structural properties of this polyanionic polysaccharide. Now a dynamic covalent selection approach is used to identify a new ligand for heparin, assembled from extremely simple building blocks. The amplified molecule strongly binds to heparin (K D in the low μm range, ITC) by a combination of electrostatic, hydrogen bonding, and CH–π interactions as shown by NMR and molecular modeling. Moreover, this ligand reverts the inhibitory effect of heparin within an enzymatic cascade reaction related to blood coagulation. This study demonstrates the power of dynamic covalent chemistry for the discovery of new modulators of biologically relevant glycosaminoglycans. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Publisher version (URL)https://doi.org/10.1002/anie.201806770
URIhttp://hdl.handle.net/10261/181442
DOI10.1002/anie.201806770
Appears in Collections:(IQAC) Artículos
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