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Literature DB >> 20379591

On-resin peptide macrocyclization using thiol-ene click chemistry.

Alex A Aimetti¹, Richard K Shoemaker, Chien-Chi Lin, Kristi S Anseth.

Abstract

A versatile and rapid synthetic strategy has been developed for the on-resin cyclization of peptides using thiol-ene photochemistry. This unique method exploits the thiol group of natural cysteine amino acids and allows for various alkenes to be incorporated orthogonal to the peptide backbone.

Entities: Chemical Disease Gene Species

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Year: 2010 PMID： 20379591 PMCID： PMC3969419 DOI： 10.1039/c001375g

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

14 in total

1. Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition.

Authors: Sreenivas Punna; Jane Kuzelka; Qian Wang; M G Finn
Journal: Angew Chem Int Ed Engl Date: 2005-04-08 Impact factor: 15.336

2. Backbone cyclization: A new method for conferring conformational constraint on peptides.

Authors: C Gilon; D Halle; M Chorev; Z Selinger; G Byk
Journal: Biopolymers Date: 1991-05 Impact factor: 2.505

3. Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides.

Authors: Rushia A Turner; Allen G Oliver; R Scott Lokey
Journal: Org Lett Date: 2007-10-23 Impact factor: 6.005

4. Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization.

Authors: Brian D Polizzotti; Benjiman D Fairbanks; Kristi S Anseth
Journal: Biomacromolecules Date: 2008-03-20 Impact factor: 6.988

5. Cyclic RGD peptide analogues as antiplatelet antithrombotics.

Authors: P L Barker; S Bullens; S Bunting; D J Burdick; K S Chan; T Deisher; C Eigenbrot; T R Gadek; R Gantzos; M T Lipari
Journal: J Med Chem Date: 1992-05-29 Impact factor: 7.446

6. Norbornene-constrained cyclic peptides with hairpin architecture: design, synthesis, conformation, and membrane ion transport.

Authors: D Ranganathan; V Haridas; S Kurur; R Nagaraj; E Bikshapathy; A C Kunwar; A V Sarma; M Vairamani
Journal: J Org Chem Date: 2000-01-28 Impact factor: 4.354

7. Direct inhibition of the NOTCH transcription factor complex.

Authors: Raymond E Moellering; Melanie Cornejo; Tina N Davis; Cristina Del Bianco; Jon C Aster; Stephen C Blacklow; Andrew L Kung; D Gary Gilliland; Gregory L Verdine; James E Bradner
Journal: Nature Date: 2009-11-12 Impact factor: 49.962

8. Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry.

Authors: Kato L Killops; Luis M Campos; Craig J Hawker
Journal: J Am Chem Soc Date: 2008-03-20 Impact factor: 15.419

9. Activation of apoptosis in vivo by a hydrocarbon-stapled BH3 helix.

Authors: Loren D Walensky; Andrew L Kung; Iris Escher; Thomas J Malia; Scott Barbuto; Renee D Wright; Gerhard Wagner; Gregory L Verdine; Stanley J Korsmeyer
Journal: Science Date: 2004-09-03 Impact factor: 47.728

10. Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis.

Authors: Michele Fiore; Alberto Marra; Alessandro Dondoni
Journal: J Org Chem Date: 2009-06-05 Impact factor: 4.354

18 in total

Review 1. Contemporary strategies for peptide macrocyclization.

Authors: Christopher J White; Andrei K Yudin
Journal: Nat Chem Date: 2011-06-23 Impact factor: 24.427

2. 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

3. N-terminus 4-Chloromethyl Thiazole Peptide as a Macrocyclization Tool in the Synthesis of Cyclic Peptides: Application to the Synthesis of Conformationally Constrained RGD-Containing Integrin Ligands.

Authors: Adel Nefzi; Jason E Fenwick
Journal: Tetrahedron Lett Date: 2011-02-16 Impact factor: 2.415

4. Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation.

Authors: Xiaodong Shi; Yinghuan Liu; Rongtong Zhao; Zigang Li
Journal: J Vis Exp Date: 2018-08-01 Impact factor: 1.355

5. Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.

Authors: Stefan J McCarver; Jennifer X Qiao; Joseph Carpenter; Robert M Borzilleri; Michael A Poss; Martin D Eastgate; Michael M Miller; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2016-11-17 Impact factor: 15.336

6. On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael "Click" Acceptor.

Authors: Bryan P Sutherland; Bassil M El-Zaatari; Nicole I Halaszynski; Jonathan M French; Shi Bai; Christopher J Kloxin
Journal: Bioconjug Chem Date: 2018-11-26 Impact factor: 4.774

7. Design of functionalized cyclic peptides through orthogonal click reactions for cell culture and targeting applications.

Authors: Paige J LeValley; Elisa M Ovadia; Christopher A Bresette; Lisa A Sawicki; Emanual Maverakis; Shi Bai; April M Kloxin
Journal: Chem Commun (Camb) Date: 2018-06-19 Impact factor: 6.222

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

Authors: Alex A Aimetti; Kristen R Feaver; Kristi S Anseth
Journal: Chem Commun (Camb) Date: 2010-06-15 Impact factor: 6.222

9. Expanding the Thiol-X Toolbox: Photoinitiation and Materials Application of the Acid-Catalyzed Thiol-ene (ACT) Reaction.

Authors: Bryan P Sutherland; Mukund Kabra; Christopher J Kloxin
Journal: Polym Chem Date: 2021-01-13 Impact factor: 5.582

10. Design of thiol-ene photoclick hydrogels using facile techniques for cell culture applications†Electronic supplementary information (ESI) available. See DOI: 10.1039/c4bm00187gClick here for additional data file.

Authors: Lisa A Sawicki; April M Kloxin
Journal: Biomater Sci Date: 2014-09-01 Impact factor: 6.843