Literature DB >> 16178569

Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides.

Jan H van Maarseveen1, W Seth Horne, M Reza Ghadiri.   

Abstract

[reaction: see text] A tandem dimerization-macrocyclization approach using 1,3-dipolar azide-alkyne cycloaddition reactions has been employed in the facile and convergent solution phase syntheses of C2 symmetric cyclic peptide scaffolds bearing triazole epsilon2-amino acids as dipeptide surrogates.

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Year:  2005        PMID： 16178569      PMCID： PMC1829324          DOI： 10.1021/ol0518028

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

1.  A Synthetic Pore-Mediated Transmembrane Transport of Glutamic Acid This work is supported by a grant from the National Institutes of Health (Grant: GM52190).

Authors:  Jorge Sánchez-Quesada; Hui Sun Kim; M. Reza Ghadiri
Journal:  Angew Chem Int Ed Engl       Date:  2001-07-02       Impact factor: 15.336

2.  Self-Assembly of Cyclic Peptides into Nanotubes and Then into Highly Anisotropic Crystalline Materials This work was supported by FCAR Québec.

Authors:  David Gauthier; Pierre Baillargeon; Marc Drouin; Yves L. Dory
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

3.  Heterocyclic peptide backbone modifications in an alpha-helical coiled coil.

Authors:  W Seth Horne; Maneesh K Yadav; C David Stout; M Reza Ghadiri
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

4.  Peptide-polymer hybrid nanotubes.

Authors:  Julien Couet; J D Jeyaprakash S Samuel; Alexey Kopyshev; Svetlana Santer; Markus Biesalski
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-20       Impact factor: 15.336

5.  Self-assembling organic nanotubes from enantiopure cyclo-N,N'-linked oligoureas: design, synthesis, and crystal structure.

Authors:  Vincent Semetey; Claude Didierjean; Jean-Paul Briand; André Aubry; Gilles Guichard
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-03       Impact factor: 15.336

6.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.

Authors:  Christian W Tornøe; Caspar Christensen; Morten Meldal
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

7.  A heterocyclic peptide nanotube.

Authors:  W Seth Horne; C David Stout; M Reza Ghadiri
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

8.  Enhancement of solubility by temporary dimethoxybenzyl-substitution of peptide bonds. Towards the synthesis of defined oligomers of alanine and of lysyl-glutamyl-glycine.

Authors:  J Blaakmeer; T Tijsse-Klasen; G I Tesser
Journal:  Int J Pept Protein Res       Date:  1991-06

9.  Palladium-catalyzed hydroxycarbonylation of aryl and vinyl halides or triflates by acetic anhydride and formate anions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi; Antonella Goggiamani
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

10.  Self-assembling peptide nanotubes from enantiomeric pairs of cyclic peptides with alternating D and L amino acid residues.

Authors:  Katri Rosenthal-Aizman; Gunnar Svensson; Anders Undén
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419
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  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.  Solid-phase peptide head-to-side chain cyclodimerization: discovery of C(2)-symmetric cyclic lactam hybrid α-melanocyte-stimulating hormone (MSH)/agouti-signaling protein (ASIP) analogues with potent activities at the human melanocortin receptors.

Authors:  Alexander V Mayorov; Minying Cai; Erin S Palmer; Zhihua Liu; James P Cain; Josef Vagner; Dev Trivedi; Victor J Hruby
Journal:  Peptides       Date:  2010-08-03       Impact factor: 3.750

Review 3.  Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide-Alkyne Cycloaddition.

Authors:  Chad J Pickens; Stephanie N Johnson; Melissa M Pressnall; Martin A Leon; Cory J Berkland
Journal:  Bioconjug Chem       Date:  2018-02-01       Impact factor: 4.774

4.  Generation of candidate ligands for nicotinic acetylcholine receptors via in situ click chemistry with a soluble acetylcholine binding protein template.

Authors:  Neil P Grimster; Bernhard Stump; Joseph R Fotsing; Timo Weide; Todd T Talley; John G Yamauchi; Ákos Nemecz; Choel Kim; Kwok-Yiu Ho; K Barry Sharpless; Palmer Taylor; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-04-06       Impact factor: 15.419

5.  Inter- versus intra-molecular cyclization of tripeptides containing tetrahydrofuran amino acids: a density functional theory study on kinetic control.

Authors:  N V Suresh Kumar; U Deva Priyakumar; Harjinder Singh; Saumya Roy; Tushar Kanti Chakraborty
Journal:  J Mol Model       Date:  2012-01-12       Impact factor: 1.810

6.  Enzymatic glycosylation of triazole-linked GlcNAc/Glc-peptides: synthesis, stability and anti-HIV activity of triazole-linked HIV-1 gp41 glycopeptide C34 analogues.

Authors:  Wei Huang; Stan Groothuys; Alonso Heredia; Brian H M Kuijpers; Floris P J T Rutjes; Floris L van Delft; Lai-Xi Wang
Journal:  Chembiochem       Date:  2009-05-04       Impact factor: 3.164

7.  Probing the bioactive conformation of an archetypal natural product HDAC inhibitor with conformationally homogeneous triazole-modified cyclic tetrapeptides.

Authors:  W Seth Horne; Christian A Olsen; John M Beierle; Ana Montero; M Reza Ghadiri
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues.

Authors:  John M Beierle; W Seth Horne; Jan H van Maarseveen; Beatrice Waser; Jean Claude Reubi; M Reza Ghadiri
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Peptide tertiary structure nucleation by side-chain crosslinking with metal complexation and double "click" cycloaddition.

Authors:  Oscar Torres; Deniz Yüksel; Matt Bernardina; Krishna Kumar; Dennis Bong
Journal:  Chembiochem       Date:  2008-07-21       Impact factor: 3.164

10.  Peptide cyclization and cyclodimerization by Cu(I)-mediated azide-alkyne cycloaddition.

Authors:  Reshma Jagasia; Justin M Holub; Markus Bollinger; Kent Kirshenbaum; M G Finn
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354
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