Combinatorial Library Screening Coupled to Mass Spectrometry to Identify Valuable Cyclic Peptides. Issue 2 (2nd June 2016)

• Record Type: Journal Article
• Authors: Camperi, Silvia A.; Giudicessi, Silvana L.; Martínez‐Ceron, María C.; Gurevich‐Messina, Juan M.; Saavedra, Soledad L.; Acosta, Gerardo; Cascone, Osvaldo; Erra‐Balsells, Rosa; Albericio, Fernando
• Editors: Mahal, Lara; Romesberg, Floyd; Shah, Kavita; Shamu, Caroline; Strano, Michael S.; Thomas, Craig
• Is Part Of: Current protocols in chemical biology. Volume 8:Issue 2(2016)
• Page Start: 109
• Page End: 130
• Publication Date: 2016-06-02
• Subjects: affinity -- ChemMatrix -- combinatorial -- depsipeptides -- MALDI MS; Biochemistry -- Laboratory manuals; Chemical Phenomena; Biochemistry; Periodicals; Laboratory manuals; 572.078
• DOI: 10.1002/cpch.2
• Languages: English
• ISSNs: 2160-4762

Abstract

Abstract: Combinatorial library screening coupled to mass spectrometry (MS) analysis is a practical approach to identify useful peptides. Cyclic peptides can have high biological activity, selectivity, and affinity for target proteins, and high stability against proteolytic degradation. Here we describe two strategies to prepare combinatorial libraries suitable for MS analysis to accelerate the discovery of cyclic peptide structures. Both approaches use ChemMatrix resin and the linker 4‐hydroxymethylbenzoic acid. One strategy involves the synthesis of a one‐bead–two‐peptides library in which each bead contains both the cyclic peptide and its linear counterpart to facilitate MS analysis. The other protocol is based on the synthesis of a cyclic depsipeptide library in which a glycolamidic ester group is incorporated by adding glycolic acid. After library screening, the ring is opened and the peptide is released simultaneously for subsequent MS analysis. © 2016 by John Wiley & Sons, Inc.