Literature DB >> 20552127

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

Alex A Aimetti1, Kristen R Feaver, Kristi S Anseth.   

Abstract

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.

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Year:  2010        PMID： 20552127      PMCID： PMC3961633          DOI： 10.1039/c0cc01292k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  19 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry.

Authors:  Dirk T S Rijkers; G Wilma van Esse; Remco Merkx; Arwin J Brouwer; Hans J F Jacobs; Roland J Pieters; Rob M J Liskamp
Journal:  Chem Commun (Camb)       Date:  2005-08-19       Impact factor: 6.222

3.  Translating peptides into small molecules.

Authors:  Gerd Hummel; Ulrich Reineke; Ulf Reimer
Journal:  Mol Biosyst       Date:  2006-08-24

4.  Synthetic peptide vaccine design: synthesis and properties of a high-density multiple antigenic peptide system.

Authors:  J P Tam
Journal:  Proc Natl Acad Sci U S A       Date:  1988-08       Impact factor: 11.205

Review 5.  Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors.

Authors:  Mathai Mammen; Seok-Ki Choi; George M Whitesides
Journal:  Angew Chem Int Ed Engl       Date:  1998-11-02       Impact factor: 15.336

6.  "Clicking" polymer brushes with thiol-yne chemistry: indoors and out.

Authors:  Ryan M Hensarling; Vanessa A Doughty; Justin W Chan; Derek L Patton
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

7.  Versatile conjugation of octreotide to dendrimers by cycloaddition ("click") chemistry to yield high-affinity multivalent cyclic Peptide dendrimers.

Authors:  Cheng-Bin Yim; Otto C Boerman; Monique de Visser; Marion de Jong; Annemarie C Dechesne; Dirk T S Rijkers; Rob M J Liskamp
Journal:  Bioconjug Chem       Date:  2009-07       Impact factor: 4.774

8.  Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction.

Authors:  Michael M Madden; Claudia I Rivera Vera; Wenjiao Song; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2009-08-13       Impact factor: 6.222

9.  Sequential phosphine-catalyzed, nucleophilic thiol-ene/radical-mediated thiol-yne reactions and the facile orthogonal synthesis of polyfunctional materials.

Authors:  Justin W Chan; Charles E Hoyle; Andrew B Lowe
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

10.  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.

Authors:  Ingrid Dijkgraaf; Anneloes Y Rijnders; Annemieke Soede; Annemarie C Dechesne; G Wilma van Esse; Arwin J Brouwer; Frans H M Corstens; Otto C Boerman; Dirk T S Rijkers; Rob M J Liskamp
Journal:  Org Biomol Chem       Date:  2007-01-29       Impact factor: 3.876
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  5 in total

1.  Exhaustive glycosylation, PEGylation, and glutathionylation of a [G4]-ene(48) dendrimer via photoinduced thiol-ene coupling.

Authors:  Mauro Lo Conte; Maxwell J Robb; Yvonne Hed; Alberto Marra; Michael Malkoch; Craig J Hawker; Alessandro Dondoni
Journal:  J Polym Sci A Polym Chem       Date:  2011-10-15       Impact factor: 2.702

2.  Forging isopeptide bonds using thiol-ene chemistry: site-specific coupling of ubiquitin molecules for studying the activity of isopeptidases.

Authors:  Ellen M Valkevich; Robert G Guenette; Nicholas A Sanchez; Yi-chen Chen; Ying Ge; Eric R Strieter
Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

3.  Facile functionalization of polyesters through thiol-yne chemistry for the design of degradable, cell-penetrating and gene delivery dual-functional agents.

Authors:  Zhonghai Zhang; Lichen Yin; Yunxiang Xu; Rong Tong; Yanbing Lu; Jie Ren; Jianjun Cheng
Journal:  Biomacromolecules       Date:  2012-10-26       Impact factor: 6.988

Review 4.  Photochemical Methods for Peptide Macrocyclisation.

Authors:  Laetitia Raynal; Nicholas C Rose; James R Donald; Christopher D Spicer
Journal:  Chemistry       Date:  2020-10-27       Impact factor: 5.236

5.  Bioorthogonal Click Chemistry: An Indispensable Tool to Create Multifaceted Cell Culture Scaffolds.

Authors:  Malar A Azagarsamy; Kristi S Anseth
Journal:  ACS Macro Lett       Date:  2012-12-14       Impact factor: 6.903
  5 in total

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