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

被引:36
作者
Demizu, Yosuke [1 ,2 ]
Oba, Makoto [3 ]
Okitsu, Koyo [2 ,4 ]
Yamashita, Hiroko [2 ,4 ]
Misawa, Takashi [2 ]
Tanaka, Masakazu [3 ]
Kurihara, Masaaki [2 ,4 ]
Gellman, Samuel H. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53707 USA
[2] Natl Inst Hlth Sci Setagaya, Tokyo 1588501, Japan
[3] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
[4] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Yokohama, Kanagawa 2268501, Japan
基金
美国国家科学基金会;
关键词
ALPHA-HELIX MIMICRY; INTRACELLULAR DELIVERY; POLYPLEX MICELLES; DESIGN; FOLDAMERS; MOLECULES; ANTIBACTERIAL; TRANSLOCATION; TRANSFECTION; TRANSPORTERS;
D O I
10.1039/c5ob00389j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cyclic beta-amino acid (APC(Gu)) bearing a side-chain guanidinium group has been developed. The APC(Gu) residue was incorporated into an alpha/beta-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 alpha-peptide.
引用
收藏
页码:5617 / 5620
页数:4
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