Synthesis and gelation properties of a new class of α-amino acid-based sector block dendrons

被引:17
|
作者
Chow, HF [1 ]
Zhang, J [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
dendrimers; amino acid-based dendrimers; organogelators;
D O I
10.1016/j.tet.2005.08.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series of alpha-amino acid-based sector block dendrons containing alanine, phenylalanine, and valine dendritic sectors was prepared by a solution phase peptide coupling methodology. The structures of the dendrons were fully characterized by nuclear magnetic resonance and mass spectroscopy and by optical polarimetry, and their purities were determined by size exclusion chromatography. Some of the dendrons, especially those containing phenylalanine residues, were found to form strong physical gels with aromatic solvents. The gelation mechanism was further investigated by infra-red and circular dichroism spectroscopy. It was found that both inter-molecular hydrogen bonding and aromatic pi-pi stacking interactions were the main driving forces for gelation. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11279 / 11290
页数:12
相关论文
共 50 条
  • [21] Chemo-enzymatic synthesis of amino acid-based surfactants
    BBSRC Inst of Food Research, Reading, United Kingdom
    JAOCS, Journal of the American Oil Chemists' Society, 1997, 74 (07): : 879 - 886
  • [22] An amino acid-based swift synthesis of zinc oxide nanostructures
    Subramanian, Navaladian
    Al Ghaferi, Amal
    RSC ADVANCES, 2014, 4 (09): : 4371 - 4378
  • [23] Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
    Paulina Juszczyk
    Regina Kasprzykowska
    Aleksandra S. Kołodziejczyk
    Letters in Peptide Science, 2003, 10 (2): : 79 - 82
  • [24] Chemo-enzymatic synthesis of amino acid-based surfactants
    Valivety, R
    Jauregi, P
    Gill, I
    Vulfson, E
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1997, 74 (07) : 879 - 886
  • [25] Amino acid-based dithiazines: Synthesis and photofragmentation of their benzaldehyde adducts
    Kurchan, AN
    Kutateladze, AG
    ORGANIC LETTERS, 2002, 4 (23) : 4129 - 4131
  • [26] Development of amino acid-based surfactants: from synthesis to applications
    Holmberg, Krister
    Bilen, Frida
    Bordes, Romain
    CURRENT OPINION IN COLLOID & INTERFACE SCIENCE, 2025, 75
  • [27] Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
    Juszczyk, P
    Kasprzykowska, R
    Kolodziejczyk, AS
    LETTERS IN PEPTIDE SCIENCE, 2003, 10 (02): : 79 - 82
  • [28] Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases
    Whalen, LJ
    McEvoy, KA
    Halcomb, RL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (02) : 301 - 304
  • [29] New Salicilic Acid-Based Azo Dyes Synthesis, Characterization and Colour Properties
    Popa, Simona
    Padure, Mirabela
    Gruescu, Corina M.
    Boran, Sorina
    REVISTA DE CHIMIE, 2015, 66 (12): : 2021 - 2027
  • [30] Synthesis and cation binding properties of new bile acid-based crown ethers
    Maitra, U
    D'Souza, LJ
    Kumar, PV
    SUPRAMOLECULAR CHEMISTRY, 1998, 10 (02) : 97 - 106