Issue 9, 2018

Water soluble hydrophobic peptoids via a minor backbone modification

Abstract

Peptoids – oligomers of N-substituted glycine – are an important class of peptide mimics that are widely used in areas ranging from biology and medicine to metal binding and catalysis. The utility of peptoids, however, especially for applications in aqueous solutions, is often hampered by the hydrophobic nature of their sequences dictated by structural and functional requirements. Herein we describe a simple method to solubilize hydrophobic peptoids in water without modifying their original sequences, via the insertion of biocompatible and low cost piperazine or homopiperazine groups at the N- or C-terminus of the peptoid backbone. We show that our method can be applied for the production of α-, β- and azapeptoids, which display high water solubility for long periods of time. Moreover, circular dichroism (CD) spectroscopy revealed that the incorporation of piperazine groups within α-peptoids, having chiral naphthyl monomers, β-peptoids and unstructured azapeptoids results in peptoids that exhibit high conformational order in water.

Graphical abstract: Water soluble hydrophobic peptoids via a minor backbone modification

Supplementary files

Article information

Article type
Paper
Submitted
27 Nov 2017
Accepted
25 Jan 2018
First published
25 Jan 2018

Org. Biomol. Chem., 2018,16, 1480-1488

Water soluble hydrophobic peptoids via a minor backbone modification

C. M. Darapaneni, P. J. Kaniraj and G. Maayan, Org. Biomol. Chem., 2018, 16, 1480 DOI: 10.1039/C7OB02928D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements