Issue 20, 2015
From the journal:

Organic & Biomolecular Chemistry

A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides†

Yosuke Demizu,*ab   Makoto Oba,c   Koyo Okitsu,bd   Hiroko Yamashita,bd   Takashi Misawa,b   Masakazu Tanaka,c   Masaaki Kuriharabd  and  Samuel H. Gellmana  

* Corresponding authors

a Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, WI 53707, USA
E-mail: demizu@nihs.go.jp

b National Institute of Health Sciences Setagaya, Tokyo 1588501, Japan

c Graduate School of Biomedical Sciences, Nagasaki University Bunkyo-machi, Nagasaki 8528521, Japan

d Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Japan

Abstract

A cyclic β-amino acid (APCGu) bearing a side-chain guanidinium group has been developed. The APCGu residue was incorporated into an α/β-peptide based on the Tat(47–57) fragment, leading to an oligomer with substantial helicity in methanol that enters HeLa cells much more readily than does the corresponding Tat α-peptide.

Graphical abstract: A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

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Article information

DOI
https://doi.org/10.1039/C5OB00389J
Article type
Communication
Submitted
26 Feb 2015
Accepted
13 Apr 2015
First published
14 Apr 2015
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2015,13, 5617-5620

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A preorganized β-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

Y. Demizu, M. Oba, K. Okitsu, H. Yamashita, T. Misawa, M. Tanaka, M. Kurihara and S. H. Gellman, Org. Biomol. Chem., 2015, 13, 5617 DOI: 10.1039/C5OB00389J

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