Extraordinary metabolic stability of peptides containing α-aminoxy acids

被引:25
作者
Chen, Fei [1 ]
Ma, Bin [2 ]
Yang, Zong-Chang [1 ]
Lin, Ge [2 ]
Yang, Dan [1 ]
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[2] Chinese Univ Hong Kong, Sch Biomed Sci, Shatin, Hong Kong, Peoples R China
关键词
Metabolism; Peptides; Stability; Aminoxy acid; BETA-PEPTIDES; BIOLOGICAL STABILITY; CYCLIC HEXAPEPTIDE; CHLORIDE-ION; IN-VITRO; FOLDAMERS; RECEPTOR; TURNS; HELICES; CHANNELS;
D O I
10.1007/s00726-011-1095-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
The metabolic stability of peptides containing a mixed sequence of alpha-aminoxy acids and alpha-amino acids is significantly improved compared to peptides composed of only natural alpha-amino acids. The introduction of an alpha-aminoxy acid into peptide chain dramatically improves the stability of the amide bonds immediately before and after it. These peptides containing alpha-aminoxy acids represent excellent structural scaffold for the design of metabolically stable and biologically active peptides.
引用
收藏
页码:499 / 503
页数:5
相关论文
共 26 条
[1]
Sophistication of foldamer form and function in vitro and in vivo [J].
Bautista, Arjel D. ;
Craig, Cody J. ;
Harker, Elizabeth A. ;
Schepartz, Alanna .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2007, 11 (06) :685-692
[2]
γ4-aminoxy peptides as new peptidomimetic foldamers [J].
Chen, F ;
Zhu, NY ;
Yang, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) :15980-15981
[3]
Synthesis and conformational studies of γ-aminoxy peptides [J].
Chen, Fei ;
Song, Ke-Sheng ;
Wu, Yun-Dong ;
Yang, Dan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :743-755
[4]
β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[5]
Frackenpohl J, 2001, CHEMBIOCHEM, V2, P445, DOI 10.1002/1439-7633(20010601)2:6<445::AID-CBIC445>3.3.CO
[6]
2-I
[7]
Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[8]
PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267
[9]
Recent developments in the synthesis of amino acids and analogues for foldamers study [J].
Haldar, Debasish .
CURRENT ORGANIC SYNTHESIS, 2008, 5 (01) :61-80
[10]
Enzymatic degradation of β- and mixed α,β-oligopeptides [J].
Heck, Tobias ;
Limbach, Michael ;
Geueke, Birgit ;
Zacharias, Martin ;
Gardiner, James ;
Kohler, Hans-Peter E. ;
Seebach, Dieter .
CHEMISTRY & BIODIVERSITY, 2006, 3 (12) :1325-1348