Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry

被引：19

作者：

Ramos-Soriano, Javier ^{[1
,2
]}

Reina, Jose J. ^{[2
]}

Perez-Sanchez, Alfonso ^{[1
]}

Illescas, Beatriz M. ^{[1
]}

Rojo, Javier ^{[2
]}

Martin, Nazario ^{[1
,3
]}

机构：

[1] Univ Complutense Madrid, Dept Quim Organ, Fac CC Quim, Av Complutense S-N, E-28040 Madrid, Spain

[2] Univ Seville, CSIC, IIQ, Glycosyst Lab, Av Amer Vespucio 49, Seville 41092, Spain

[3] IMDEA Nanosci, Campus Cantoblanco, Madrid 28049, Spain

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 69期

基金：

欧洲研究理事会;

关键词：

CRYSTAL-STRUCTURE; FUNCTIONALIZATION; CYCLOADDITION; FULLERENES; FRAMEWORK;

D O I：

10.1039/c6cc05484f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a new highly symmetric hexakis adduct of C-60 appended with 12 cyclooctyne moieties has been carried out. This compound has been used for the copper-free strain-promoted cycloaddition reaction to a series of azides with excellent yields. This strategy for the obtention of clicked adducts of [60]fullerene is of special interest for biological applications.

引用

页码：10544 / 10546

页数：3

共 30 条

[1] A comparative study of bioorthogonal reactions with azides
Agard, Nicholas J.
Baskin, Jeremy M.
Prescher, Jennifer A.
Lo, Anderson
Bertozzi, Carolyn R.
[J]. ACS CHEMICAL BIOLOGY, 2006, 1 (10) : 644 - 648
[2] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems
Agard, NJ
Prescher, JA
Bertozzi, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15046 - 15047
[3] Copper-free click chemistry for dynamic in vivo imaging
Baskin, Jeremy M.
Prescher, Jennifer A.
Laughlin, Scott T.
Agard, Nicholas J.
Chang, Pamela V.
Miller, Isaac A.
Lo, Anderson
Codelli, Julian A.
Bertozzi, Carolyn R.
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) : 16793 - 16797
[4] Catalytic Synergism in a C60IL10TEMPO2 Hybrid in the Efficient Oxidation of Alcohols
Beejapur, Hazi Ahmad
Campisciano, Vincenzo
Giacalone, Francesco
Gruttadauria, Michelangelo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (01) : 51 - 58
[5] An optically-active liquid-crystalline hexa-adduct of [60]fullerene which displays supramolecular helical organization
Campidelli, Stephane
Brandmueller, Torsten
Hirsch, Andreas
Saez, Isabel M.
Goodby, John W.
Deschenaux, Robert
[J]. CHEMICAL COMMUNICATIONS, 2006, (41) : 4282 - 4284
[6] Fullerene-Ionic-Liquid Conjugates: A New Class of Hybrid Materials with Unprecedented Properties
Campisciano, Vincenzo
La Parola, Valeria
Liotta, Leonarda F.
Giacalone, Francesco
Gruttadauria, Michelangelo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (08) : 3327 - 3334
[7] Synthesis of Dodecavalent Fullerene-Based Glycoclusters and Evaluation of Their Binding Properties towards a Bacterial Lectin
Cecioni, Samy
Oerthel, Vincent
Iehl, Julien
Holler, Michel
Goyard, David
Praly, Jean-Pierre
Imberty, Anne
Nierengarten, Jean-Francois
Vidal, Sebastien
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (11) : 3252 - 3261
[8] A liquid-crystalline hexa-adduct of [60]fullerene
Chuard, T
Deschenaux, R
Hirsch, A
Schönberger, H
[J]. CHEMICAL COMMUNICATIONS, 1999, (20) : 2103 - 2104
[9] The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition
Durka, Maxime
Buffet, Kevin
Iehl, Julien
Holler, Michel
Nierengarten, Jean-Francois
Vincent, Stephane P.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) : 641 - 651
[10] The functional valency of dodecamannosylated fullerenes with Escherichia coli FimH-towards novel bacterial antiadhesives
Durka, Maxime
Buffet, Kevin
Iehl, Julien
Holler, Michel
Nierengarten, Jean-Francois
Taganna, Joemar
Bouckaert, Julie
Vincent, Stephane P.
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (04) : 1321 - 1323

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