Literature DB >> 19753366

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

Michael M Madden1, Claudia I Rivera Vera, Wenjiao Song, Qing Lin.   

Abstract

We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

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Year:  2009        PMID： 19753366      PMCID： PMC2765658          DOI： 10.1039/b912094g

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


  23 in total

1.  Toward proteomimetics: terphenyl derivatives as structural and functional mimics of extended regions of an alpha-helix.

Authors:  B P Orner; J T Ernst; A D Hamilton
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Aib-rich peptides containing lactam-bridged side chains as models of the 3(10)-helix.

Authors:  E Schievano; A Bisello; M Chorev; A Bisol; S Mammi; E Peggion
Journal:  J Am Chem Soc       Date:  2001-03-28       Impact factor: 15.419

3.  Using an azobenzene cross-linker to either increase or decrease peptide helix content upon trans-to-cis photoisomerization.

Authors:  Daniel G Flint; Janet R Kumita; Oliver S Smart; G Andrew Woolley
Journal:  Chem Biol       Date:  2002-03

4.  Effective stabilisation of alpha-helical structures in short peptides with acetylenic cross-linking agents.

Authors:  Kazuhisa Fujimoto; Natsuko Oimoto; Kahori Katsuno; Masahiko Inouye
Journal:  Chem Commun (Camb)       Date:  2004-05-10       Impact factor: 6.222

5.  A highly stable short alpha-helix constrained by a main-chain hydrogen-bond surrogate.

Authors:  Ross N Chapman; Gianluca Dimartino; Paramjit S Arora
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

6.  A stapled BID BH3 helix directly binds and activates BAX.

Authors:  Loren D Walensky; Kenneth Pitter; Joel Morash; Kyoung Joon Oh; Scott Barbuto; Jill Fisher; Eric Smith; Gregory L Verdine; Stanley J Korsmeyer
Journal:  Mol Cell       Date:  2006-10-20       Impact factor: 17.970

7.  Development of a series of cross-linking agents that effectively stabilize alpha-helical structures in various short peptides.

Authors:  Kazuhisa Fujimoto; Masaoki Kajino; Masahiko Inouye
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Stabilization of folded peptide and protein structures via distance matching with a long, rigid cross-linker.

Authors:  Fuzhong Zhang; Oleg Sadovski; Steven J Xin; G Andrew Woolley
Journal:  J Am Chem Soc       Date:  2007-10-26       Impact factor: 15.419

9.  Reactivation of the p53 tumor suppressor pathway by a stapled p53 peptide.

Authors:  Federico Bernal; Andrew F Tyler; Stanley J Korsmeyer; Loren D Walensky; Gregory L Verdine
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

10.  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
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  16 in total

1.  Synthesis of cell-permeable stapled peptide dual inhibitors of the p53-Mdm2/Mdmx interactions via photoinduced cycloaddition.

Authors:  Michael M Madden; Avinash Muppidi; Zhenyu Li; Xiaolong Li; Jiandong Chen; Qing Lin
Journal:  Bioorg Med Chem Lett       Date:  2011-01-07       Impact factor: 2.823

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

Authors:  Alex A Aimetti; Richard K Shoemaker; Chien-Chi Lin; Kristi S Anseth
Journal:  Chem Commun (Camb)       Date:  2010-04-08       Impact factor: 6.222

3.  A bioorthogonal chemistry strategy for probing protein lipidation in live cells.

Authors:  Wenjiao Song; Zhipeng Yu; Michael M Madden; Qing Lin
Journal:  Mol Biosyst       Date:  2010-04-30

4.  Synthesis of cell-permeable stapled BH3 peptide-based Mcl-1 inhibitors containing simple aryl and vinylaryl cross-linkers.

Authors:  Avinash Muppidi; Kenichiro Doi; Carlo P Ramil; Hong-Gang Wang; Qing Lin
Journal:  Tetrahedron       Date:  2014-10-21       Impact factor: 2.457

Review 5.  Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Acc Chem Res       Date:  2011-05-20       Impact factor: 22.384

6.  Conjugation of spermine enhances cellular uptake of the stapled peptide-based inhibitors of p53-Mdm2 interaction.

Authors:  Avinash Muppidi; Xiaolong Li; Jiandong Chen; Qing Lin
Journal:  Bioorg Med Chem Lett       Date:  2011-10-12       Impact factor: 2.823

7.  Water-Soluble Polypeptides with Elongated, Charged Side Chains Adopt Ultra-Stable Helical Conformations.

Authors:  Yanfeng Zhang; Hua Lu; Yao Lin; Jianjun Cheng
Journal:  Macromolecules       Date:  2011-09-13       Impact factor: 5.985

8.  Bridged beta(3)-peptide inhibitors of p53-hDM2 complexation: correlation between affinity and cell permeability.

Authors:  Arjel D Bautista; Jacob S Appelbaum; Cody J Craig; Julien Michel; Alanna Schepartz
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

9.  Rational design of proteolytically stable, cell-permeable peptide-based selective Mcl-1 inhibitors.

Authors:  Avinash Muppidi; Kenichiro Doi; Selvakumar Edwardraja; Eric J Drake; Andrew M Gulick; Hong-Gang Wang; Qing Lin
Journal:  J Am Chem Soc       Date:  2012-09-04       Impact factor: 15.419

Review 10.  Bioorthogonal chemistry: strategies and recent developments.

Authors:  Carlo P Ramil; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2013-12-07       Impact factor: 6.222
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