An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics

Longin, O., Van De Langemheen, H. and Liskamp, R. M.J. (2017) An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics. Bioorganic and Medicinal Chemistry, 25(18), pp. 5008-5015. (doi:10.1016/j.bmc.2017.05.038) (PMID:28583807)

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Abstract

The synthesis of a semi-orthogonally protected CycloTriVeratrilene (CTV) scaffold derivative as well as the sequential introduction of three different peptide loops onto this molecular scaffold via Cu(I)-catalyzed azide alkyne cycloaddition towards a medium-sized protein mimic is described. This approach for the construction of medium-sized protein mimics is illustrated by the synthesis of a paratope mimic of the monoclonal antibody Infliximab (Remicade®) and provides access to a range of highly pre-organized molecular constructs bearing three different peptide segments. This approach may find wide applications for development of protein-protein interaction disruptors as well as synthetic vaccines.

Item Type:Articles
Keywords:Molecular scaffold, orthogonal functionalization, peptide cyclisation, protein mimic, synthetic antibody
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert and Longin, Mr Ondrej and Van De Langemheen, Mr Helmus
Authors: Longin, O., Van De Langemheen, H., and Liskamp, R. M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Bioorganic and Medicinal Chemistry
Publisher:Elsevier
ISSN:0968-0896
ISSN (Online):1464-3391
Published Online:18 May 2017
Copyright Holders:Copyright © 2017 Elsevier Ltd.
First Published:First published in Bioorganic and Medicinal Chemistry 25(18):5008-5015
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher
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