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

Yosuke Demizu; Makoto Oba; Koyo Okitsu; Hiroko Yamashita; Takashi Misawa; Masakazu Tanaka; Masaaki Kurihara; Samuel H Gellman

doi:10.1039/c5ob00389j

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

Org Biomol Chem. 2015 May 28;13(20):5617-20. doi: 10.1039/c5ob00389j. Epub 2015 Apr 21.

Authors

Yosuke Demizu¹, Makoto Oba, Koyo Okitsu, Hiroko Yamashita, Takashi Misawa, Masakazu Tanaka, Masaaki Kurihara, Samuel H Gellman

Affiliation

¹ Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, WI 53707, USA. demizu@nihs.go.jp.

PMID: 25897867
DOI: 10.1039/c5ob00389j

Abstract

A cyclic β-amino acid (APC(Gu)) bearing a side-chain guanidinium group has been developed. The APC(Gu) 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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amino Acid Sequence
Amino Acids / chemistry*
Cell-Penetrating Peptides / chemistry*
Cell-Penetrating Peptides / metabolism*
Gene Products, tat / chemistry*
Gene Products, tat / metabolism*
Guanidine / chemistry*
HeLa Cells
Humans
Molecular Sequence Data
Protein Structure, Secondary
Sequence Homology, Amino Acid

Substances

Amino Acids
Cell-Penetrating Peptides
Gene Products, tat
Guanidine