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)

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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