Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions

被引:36
作者
Aimetti, Alex A. [1 ]
Feaver, Kristen R. [1 ]
Anseth, Kristi S. [1 ,2 ]
机构
[1] Univ Colorado, Dept Chem & Biol Engn, Boulder, CO 80309 USA
[2] Univ Colorado, Howard Hughes Med Inst, Boulder, CO 80309 USA
关键词
CLICK CHEMISTRY; PEPTIDE DENDRIMERS; CYCLOADDITION; NETWORKS; DESIGN; SYSTEM;
D O I
10.1039/c0cc01292k
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
A unique method has been developed for the formation of multivalent cyclic peptides. This procedure exploits on-resin peptide cyclization using a photoinitiated thiol-ene click reaction and subsequent clustering using thiol-yne photochemistry. Both reactions utilize the sulfhydryl group on natural cysteine amino acids to participate in the thiol-mediated reactions.
引用
收藏
页码:5781 / 5783
页数:3
相关论文
共 25 条
[1]
On-resin peptide macrocyclization using thiol-ene click chemistry [J].
Aimetti, Alex A. ;
Shoemaker, Richard K. ;
Lin, Chien-Chi ;
Anseth, Kristi S. .
CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4061-4063
[2]
CYCLIC RGD PEPTIDE ANALOGS AS ANTIPLATELET ANTITHROMBOTICS [J].
BARKER, PL ;
BULLENS, S ;
BUNTING, S ;
BURDICK, DJ ;
CHAN, KS ;
DEISHER, T ;
EIGENBROT, C ;
GADEK, TR ;
GANTZOS, R ;
LIPARI, MT ;
MUIR, CD ;
NAPIER, MA ;
PITTI, RM ;
PADUA, A ;
QUAN, C ;
STANLEY, M ;
STRUBLE, M ;
TOM, JYK ;
BURNIER, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :2040-2048
[3]
Photopolymerization of Thiol-Alkynes: Polysulfide Networks [J].
Chan, Justin W. ;
Zhou, Hui ;
Hoyle, Charles E. ;
Lowe, Andrew B. .
CHEMISTRY OF MATERIALS, 2009, 21 (08) :1579-1585
[4]
Sequential Phosphine-Catalyzed, Nucleophilic Thiol-Ene/Radical-Mediated Thiol-Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials [J].
Chan, Justin W. ;
Hoyle, Charles E. ;
Lowe, Andrew B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (16) :5751-+
[5]
Efficient synthesis of dendrimers via a thiol-yne and esterification process and their potential application in the delivery of platinum anti-cancer drugs [J].
Chen, Gaojian ;
Kumar, Jatin ;
Gregory, Andrew ;
Stenzel, Martina H. .
CHEMICAL COMMUNICATIONS, 2009, (41) :6291-6293
[6]
Synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers via 1,3-dipolar cycloaddition and their biological evaluation:: implications for tumor targeting and tumor imaging purposes [J].
Dijkgraaf, Ingrid ;
Rijnders, Anneloes Y. ;
Soede, Annemieke ;
Dechesne, Annemarie C. ;
van Esse, G. Wilma ;
Brouwer, Arwin J. ;
Corstens, Frans H. M. ;
Boerman, Otto C. ;
Rijkers, Dirk T. S. ;
Liskamp, Rob M. J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) :935-944
[7]
Thiol-Yne Photopolymerizations: Novel Mechanism, Kinetics, and Step-Growth Formation of Highly Cross-Linked Networks [J].
Fairbanks, Benjamin D. ;
Scott, Timothy F. ;
Kloxin, Christopher J. ;
Anseth, Kristi S. ;
Bowman, Christopher N. .
MACROMOLECULES, 2009, 42 (01) :211-217
[8]
"Clicking" Polymer Brushes with Thiol-yne Chemistry: Indoors and Out [J].
Hensarling, Ryan M. ;
Doughty, Vanessa A. ;
Chan, Justin W. ;
Patton, Derek L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) :14673-+
[9]
Thiol-Yne Chemistry: A Powerful Tool for Creating Highly Functional Materials [J].
Hoogenboom, Richard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (20) :3415-3417
[10]
Hummel Gerd, 2006, Mol Biosyst, V2, P499, DOI 10.1039/b611791k