β3R3-Peptides: design and synthesis of novel peptidomimetics and their self-assembling properties at the air-water interface

被引:10
|
作者
Mosca, Simone [1 ]
Dannehl, Claudia [1 ]
Moeginger, Uwe [1 ]
Brezesinski, Gerald [1 ]
Hartmann, Laura [1 ]
机构
[1] Max Planck Inst Colloids & Interfaces, D-14424 Potsdam, Germany
关键词
AMPHIPHILIC ALPHA/BETA-PEPTIDES; SOLID-PHASE SYNTHESIS; BETA-AMINO ACIDS; SECONDARY STRUCTURE; FOLDAMERS; SPECTROSCOPY; MONOLAYERS; MEMBRANES; SYSTEMS;
D O I
10.1039/c3ob41135d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study we present the design and synthesis of a novel class of peptidomimetics, the beta(3R3)-peptides. Via alternating directions of the amide bonds along beta-peptide sequences, beta(3R3)-peptides can potentially extend the structural space available to beta-peptidic foldamers. Detailed analysis at the air-water interface shows strand conformations and the formation of sheet assemblies with different degrees of crystallinity. Furthermore beta(3R3)-peptides exhibit a high proteolytic stability thus making them an interesting new class of peptidomimetics for biomedical applications.
引用
收藏
页码:5399 / 5403
页数:5
相关论文
共 50 条
  • [1] Design and synthesis of self-assembling peptides
    Ranganathan, D
    PURE AND APPLIED CHEMISTRY, 1996, 68 (03) : 671 - 674
  • [2] Synthesis of amphiphilic V-type silica nanogels and study of their self-assembling at the air-water interface
    Kazakova, V. V.
    Gorbatsevich, O. B.
    Malakhova, Yu. N.
    Buzin, A. I.
    Muzafarov, A. M.
    RUSSIAN CHEMICAL BULLETIN, 2018, 67 (11) : 2088 - 2097
  • [3] Design, synthesis, and self-assembling properties of novel triazolophanes
    Haridas, V.
    Lal, Kashmiri
    Sharma, Yogesh K.
    Upreti, Shailesh
    ORGANIC LETTERS, 2008, 10 (08) : 1645 - 1647
  • [4] Self-assembling characteristics of amphiphilic zwitterionic brush random copolymers at the air-water interface
    Kim, Jonghyun
    Kim, Jin Chul
    Minh Dinh Phan
    Kim, Heesoo
    Shin, Kwanwoo
    Ree, Moonhor
    RSC ADVANCES, 2017, 7 (20): : 11813 - 11820
  • [5] Competitive adsorption at the air-water interface from a self-assembling polymer-surfactant mixture
    Chari, K
    Seo, YS
    Satija, S
    JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (31): : 11442 - 11446
  • [6] Amphiphilic Cationic β3R3-Peptides: Membrane Active Peptidomimetics and Their Potential as Antimicrobial Agents
    Mosca, Simone
    Keller, Janos
    Azzouz, Nahid
    Wagner, Stefanie
    Titz, Alexander
    Seeberger, Peter H.
    Brezesinski, Gerald
    Hartmann, Laura
    BIOMACROMOLECULES, 2014, 15 (05) : 1687 - 1695
  • [7] Computational design and experimental validation of novel Self-Assembling Peptides
    Gautieri, A.
    Soli, L.
    Pizzi, A.
    Soncini, M.
    Baldelli, F.
    Metrangolo, P.
    EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 2019, 48 : S211 - S211
  • [8] Preparation of surface-block dendrimer by using air-water interface and its self-assembling property on gold
    Higashi, N
    Koga, T
    Kitamatsu, M
    Niwa, M
    KOBUNSHI RONBUNSHU, 2000, 57 (10) : 659 - 664
  • [9] Characterization of Surface-Active Biofilm Protein BslA in Self-Assembling Langmuir Monolayer at the Air-Water Interface
    Liu, Wei
    Li, Shanghao
    Wang, Zhuguang
    Yan, Elsa C. Y.
    Leblanc, Roger M.
    LANGMUIR, 2017, 33 (30) : 7548 - 7555
  • [10] SELF-ASSEMBLING AND CHEMICAL RESPONSIVE GOLD NANOPARTICLES STUDIED AT THE AIR-WATER INTERFACE USING SYNCHRTRON X-RAYS
    Bjornholm, T.
    Norgaard, K.
    Kjaer, K.
    Brust, M.
    ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2002, 58 : C220 - C220