17α-Ethynylestradiol Peptide Labeling by 'Click' Chemistry

被引：5
作者：
Bol'shakov, Oleg I. [1 ]
Lebedyeva, Iryna O. [1 ]
Katritzky, Alan R. [1 ,2 ]
机构：
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
[2] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 18期
关键词：
cyclization; azides; alkynes; peptides; drugs; click chemistry; MECHANISM-BASED INACTIVATION; P450S; 2B1; AZIDE; DIAZOTRANSFER; ESTRADIOL; LIGATION; IDENTIFICATION; HYALURONAN;
D O I：
10.1055/s-0032-1316702
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthesis of 17 alpha-ethynylestradiol-labeled native peptides is reported. The peptide moiety is tethered to the steroid hormone by a 1,2,3-triazole bridge formed by a CuAAC reaction in which the azido group of the peptide combines with the terminal acetylenic moiety of ethynylestradiol to link the two bioactive molecules. Thus bioconjugates containing the hormone moiety at three positions within the peptide molecule could be useful targets for hormono-enzyme interaction studies.
引用
收藏
页码：2926 / 2932
页数：7
相关论文
共 40 条
  • [11] Chemoselective Ligation and Modification Strategies for Peptides and Proteins
    Hackenberger, Christian P. R.
    Schwarzer, Dirk
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (52) : 10030 - 10074
  • [12] Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues
    Hansen, Finn K.
    Ha, Khanh
    Todadze, Ekaterina
    Lillicotch, Aaron
    Frey, Alexander
    Katritzky, Alan R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) : 7162 - 7167
  • [13] Estrogen dendrimer conjugates that preferentially activate extranuclear, nongenomic versus genomic pathways of estrogen action
    Harrington, WR
    Kim, SH
    Funk, CC
    Madak-Erdogan, Z
    Schiff, R
    Katzenellenbogen, JA
    Katzenellenbogen, BS
    [J]. MOLECULAR ENDOCRINOLOGY, 2006, 20 (03) : 491 - 502
  • [14] Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
    Himo, F
    Lovell, T
    Hilgraf, R
    Rostovtsev, VV
    Noodleman, L
    Sharpless, KB
    Fokin, VV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 210 - 216
  • [15] Immobilized triazine-type dehydrocondensing reagents for carboxamide formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl
    Hioki, Kazuhito
    Kameyama, Satomi
    Tani, Shohei
    Kunishima, Munetaka
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (05) : 825 - 828
  • [16] Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support
    Holub, JM
    Jang, HJ
    Kirshenbaum, K
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (08) : 1497 - 1502
  • [17] Peptoids on steroids:: Precise multivalent estradiol-peptidomimetic conjugates generated via azide-alkyne [3+2] cycloaddition reactions
    Holub, Justin M.
    Garabedian, Michael J.
    Kirshenbaum, Kent
    [J]. QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12): : 1175 - 1180
  • [18] Modulation of human estrogen receptor α activity by multivalent estradiol-peptidomimetic conjugates
    Holub, Justin M.
    Garabedian, Michael J.
    Kirshenbaum, Kent
    [J]. MOLECULAR BIOSYSTEMS, 2011, 7 (02) : 337 - 345
  • [19] Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI [10.1002/anie.196305651, DOI 10.1002/ANIE.196305651]
  • [20] Biotinylated anisomycin: A comparison of classical and "Click" chemistry approaches
    Inverarity, Lain A.
    Viguier, Romain F. H.
    Cohen, Philip
    Hulme, Alison N.
    [J]. BIOCONJUGATE CHEMISTRY, 2007, 18 (05) : 1593 - 1603
1234