Reversible α-helix formation controlled by a hydrogen bond surrogate

被引：29
|
作者：
Miller, Stephen E. [1 ]
Kallenbach, Neville R. [1 ]
Arora, Paramjit S. [1 ]
机构：
[1] NYU, Dept Chem, New York, NY 10003 USA
来源：
TETRAHEDRON | 2012年 / 68卷 / 23期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
Foldamer; Stabilized alpha-helix; Helix inducer; Hydrogen bond surrogate; Disulfide bridge; SOLID-PHASE SYNTHESIS; STABILITY; PEPTIDES; TRIFLUOROETHANOL; MECHANISM;
D O I：
10.1016/j.tet.2011.12.068
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Strategically placed covalent linkages have been shown to stabilize helical conformations in short peptide sequences. Here we report the synthesis of a stabilized alpha-helix that utilizes an internal disulfide linkage. Structural analysis indicates that the dynamic nature of the disulfide bridge allows for the reversible formation of an alpha-helix through oxidation and reduction reactions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4434 / 4437
页数：4
相关论文
共 50 条
  • [41] DIELECTRIC STUDIES OF HYDROGEN BOND AND OF HELIX-COIL POLYPEPTIDE STRUCTURE
    DAVIES, M
    CHEMISTRY & INDUSTRY, 1968, (35) : 1191 - &
  • [42] Polarization of Intraprotein Hydrogen Bond Is Critical to Thermal Stability of Short Helix
    Gao, Ya
    Lu, Xiaoliang
    Duan, Li L.
    Zhang, John Z. H.
    Mei, Ye
    JOURNAL OF PHYSICAL CHEMISTRY B, 2012, 116 (01): : 549 - 554
  • [43] Reversible solubilisation through hydrogen-bond-mediated assembly
    Gao, Fan
    Tan, Yichen
    Yu, Yue
    Chen, Hao
    Ma, Yuguo
    SUPRAMOLECULAR CHEMISTRY, 2011, 23 (11) : 753 - 758
  • [44] Triple Helix Formation in a Topologically Controlled DNA Nanosystem
    Yamagata, Yutaro
    Emura, Tomoko
    Hidaka, Kumi
    Sugiyama, Hiroshi
    Endo, Masayuki
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (16) : 5494 - 5498
  • [45] Diastereoselective Imine-Bond Formation through Complementary Double-Helix Formation
    Yamada, Hidekazu
    Furusho, Yoshio
    Yashima, Eiji
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) : 7250 - 7253
  • [46] The influence of cations on the formation of the intramolecular hydrogen bond in hydrogen phthalates
    Langkilde, A.
    Larsen, S.
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2000, 56 : S308 - S308
  • [47] ROLE OF EXCITED ORBITALS OF HYDROGEN ATOM IN FORMATION OF A HYDROGEN BOND
    PLOTNIKO.VG
    SHIGORIN, DN
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY,USSR, 1967, 41 (07): : 933 - &
  • [48] Formation of Reversible Clusters with Controlled Degree of Aggregation
    Lotfizadeh, Saba
    Aljama, Hassan
    Reilly, Dan
    Matsoukas, Themis
    LANGMUIR, 2016, 32 (19) : 4862 - 4867
  • [49] Reversible dimerization of acid-denatured ACBP controlled by helix A4
    Fieber, W
    Kragelund, BB
    Meldal, M
    Poulsen, FM
    BIOCHEMISTRY, 2005, 44 (05) : 1375 - 1384
  • [50] Design and Synthesis of Novel Helix Mimetics Based on the Covalent H-Bond Replacement and Amide Surrogate
    Liu, Junyang
    Tang, Shoubin
    Yan, Jia-Lei
    Ye, Tao
    MOLECULES, 2023, 28 (02):
12345