Issue 28, 2020

Development of oxetane modified building blocks for peptide synthesis

Abstract

The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported. The preparation of building blocks containing non-glycine residues at the N-terminus in a stereochemically controlled manner is challenging. Here, a practical 4-step route to such building blocks is demonstrated, through the synthesis of dipeptides containing contiguous alanine residues. The incorporation of these new derivatives at specific sites along the backbone of an alanine-rich peptide sequence containing eighteen amino acids is demonstrated via solid-phase peptide synthesis. Additionally, new methods to enable the incorporation of all 20 of the proteinogenic amino acids into such dipeptide building blocks are reported through modifications of the synthetic route (for Cys and Met) and by changes to the protecting group strategy (for His, Ser and Thr).

Graphical abstract: Development of oxetane modified building blocks for peptide synthesis

Supplementary files

Article information

Article type
Paper
Submitted
20 شوال 1441
Accepted
08 ذو القعدة 1441
First published
08 ذو القعدة 1441

Org. Biomol. Chem., 2020,18, 5400-5405

Development of oxetane modified building blocks for peptide synthesis

S. Roesner, J. D. Beadle, L. K. B. Tam, I. Wilkening, G. J. Clarkson, P. Raubo and M. Shipman, Org. Biomol. Chem., 2020, 18, 5400 DOI: 10.1039/D0OB01208D

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