Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support

被引：90
作者：
Holub, JM [1 ]
Jang, HJ [1 ]
Kirshenbaum, K [1 ]
机构：
[1] NYU, Dept Chem, New York, NY 10003 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 08期
关键词：
D O I：
10.1039/b518247f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Substituted glycine peptoid oligomers were used as substrates for azide-alkyne [ 3 + 2] cycloaddition conjugation reactions and then elaborated through additional rounds of oligomerization and cycloaddition. This novel sequential conjugation technique allowed for the generation of complex peptidomimetic products in which multiple heterogeneous pendant groups were site-specifically positioned along the oligomer scaffold. Studies of a water-soluble estradiol-ferrocene peptoid conjugate demonstrated a potential application for the modular synthesis of biosensors.
引用
收藏
页码：1497 / 1502
页数：6
相关论文
共 26 条
  • [1] Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers
    Angelo, NG
    Arora, PS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17134 - 17135
  • [2] Estrogen receptor ligands. Part 13: Dihydrobenzoxathiin SERAMs with an optimized antagonist side chain
    Blizzard, TA
    DiNinno, F
    Chen, HY
    Kim, S
    Wu, JY
    Chan, WD
    Birzin, ET
    Yang, YT
    Pal, LY
    Hayes, EC
    DaSilva, CA
    Rohrer, SP
    Schaeffer, JM
    Hammond, ML
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (17) : 3912 - 3916
  • [3] ALIPHATIC AMINO AZIDES AS KEY BUILDING-BLOCKS FOR EFFICIENT POLYAMINE SYNTHESES
    CARBONI, B
    BENALIL, A
    VAULTIER, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) : 3736 - 3741
  • [4] Convenient methods for the synthesis of ferrocene-carbohydrate conjugates
    Casas-Solvas, JM
    Vargas-Berenguel, A
    Capitán-Vallvey, LF
    Santoyo-González, F
    [J]. ORGANIC LETTERS, 2004, 6 (21) : 3687 - 3690
  • [5] Synthesis, characterization, and evaluation of ferrocene-theophylline conjugates for use in electrochemical enzyme immunoassay
    Forrow, NJ
    Foulds, NC
    Frew, JE
    Law, JT
    [J]. BIOCONJUGATE CHEMISTRY, 2004, 15 (01) : 137 - 144
  • [6] Peptide ligation through click chemistry for the generation of assembled and scaffolded peptides
    Franke, R
    Doll, C
    Eichler, J
    [J]. TETRAHEDRON LETTERS, 2005, 46 (26) : 4479 - 4482
  • [7] HERMANSON GT, 1996, BIOCONJUGATE TECHNIQ
  • [8] Incorporation of chemoselective functionalities into peptoids via solid-phase submonomer synthesis
    Horn, T
    Lee, BC
    Dill, KA
    Zuckermann, RN
    [J]. BIOCONJUGATE CHEMISTRY, 2004, 15 (02) : 428 - 435
  • [9] Click to fit: Versatile polyvalent display on a peptidomimetic scaffold
    Jang, HJ
    Fafarman, A
    Holub, JM
    Kirshenbaum, K
    [J]. ORGANIC LETTERS, 2005, 7 (10) : 1951 - 1954
  • [10] Dendrimers clicked together divergently
    Joralemon, MJ
    O'Reilly, RK
    Matson, JB
    Nugent, AK
    Hawker, CJ
    Wooley, KL
    [J]. MACROMOLECULES, 2005, 38 (13) : 5436 - 5443
123