Literature DB >> 20449477

Solid phase synthesis of hydrogen bond surrogate derived alpha-helices: resolving the case of a difficult amide coupling.

Anupam Patgiri1, Michael R Witten, Paramjit S Arora.   

Abstract

Solid phase synthesis of HBS helices involving the Fukuyama-Mitsunobu reaction and triphosgene coupling is described.

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Year:  2010        PMID： 20449477      PMCID： PMC4317285          DOI： 10.1039/c000905a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  16 in total

1.  Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase.

Authors:  Bernd Thern; Joachim Rudolph; Günther Jung
Journal:  Angew Chem Int Ed Engl       Date:  2002-07-02       Impact factor: 15.336

2.  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

3.  Enhanced metabolic stability and protein-binding properties of artificial alpha helices derived from a hydrogen-bond surrogate: application to Bcl-xL.

Authors:  Deyun Wang; Wei Liao; Paramjit S Arora
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-14       Impact factor: 15.336

4.  Solid-phase synthesis of hydrogen-bond surrogate-derived alpha-helices.

Authors:  Gianluca Dimartino; Deyun Wang; Ross N Chapman; Paramjit S Arora
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

5.  Optimized synthesis of hydrogen-bond surrogate helices: surprising effects of microwave heating on the activity of Grubbs catalysts.

Authors:  Ross N Chapman; Paramjit S Arora
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

6.  Design and synthesis of alpha-helical peptides and mimetics.

Authors:  James Garner; Margaret M Harding
Journal:  Org Biomol Chem       Date:  2007-09-07       Impact factor: 3.876

7.  In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl) carbonate and its utilization for difficult couplings in solid-phase peptide synthesis.

Authors:  E Falb; T Yechezkel; Y Salitra; C Gilon
Journal:  J Pept Res       Date:  1999-05

8.  Ns strategies: a highly versatile synthetic method for amines.

Authors:  Toshiyuki Kan; Tohru Fukuyama
Journal:  Chem Commun (Camb)       Date:  2003-11-25       Impact factor: 6.222

9.  A hydrogen bond surrogate approach for stabilization of short peptide sequences in alpha-helical conformation.

Authors:  Anupam Patgiri; Andrea L Jochim; Paramjit S Arora
Journal:  Acc Chem Res       Date:  2008-07-17       Impact factor: 22.384

10.  Inhibition of hypoxia inducible factor 1-transcription coactivator interaction by a hydrogen bond surrogate alpha-helix.

Authors:  Laura K Henchey; Swati Kushal; Ramin Dubey; Ross N Chapman; Bogdan Z Olenyuk; Paramjit S Arora
Journal:  J Am Chem Soc       Date:  2010-01-27       Impact factor: 15.419
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  13 in total

1.  Design, synthesis and protein-targeting properties of thioether-linked hydrogen bond surrogate helices.

Authors:  Andrew B Mahon; Paramjit S Arora
Journal:  Chem Commun (Camb)       Date:  2011-09-28       Impact factor: 6.222

2.  Solid-phase synthesis of short α-helices stabilized by the hydrogen bond surrogate approach.

Authors:  Anupam Patgiri; Monica Z Menzenski; Andrew B Mahon; Paramjit S Arora
Journal:  Nat Protoc       Date:  2010-10-28       Impact factor: 13.491

3.  Synthesis of hydrogen-bond surrogate α-helices as inhibitors of protein-protein interactions.

Authors:  Stephen E Miller; Paul F Thomson; Paramjit S Arora
Journal:  Curr Protoc Chem Biol       Date:  2014-06-03

4.  End-Capped α-Helices as Modulators of Protein Function.

Authors:  Andrew B Mahon; Paramjit S Arora
Journal:  Drug Discov Today Technol       Date:  2012

5.  Nucleation effects in peptide foldamers.

Authors:  Anupam Patgiri; Stephen T Joy; Paramjit S Arora
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

Review 6.  Mini review: protein-protein interactions in transcription: a fertile ground for helix mimetics.

Authors:  Danielle A Guarracino; Brooke N Bullock; Paramjit S Arora
Journal:  Biopolymers       Date:  2011-01       Impact factor: 2.505

7.  A decade review of triphosgene and its applications in organic reactions.

Authors:  Moshood O Ganiu; Binod Nepal; Joshua P Van Houten; Rendy Kartika
Journal:  Tetrahedron       Date:  2020-09-06       Impact factor: 2.457

8.  High specificity in protein recognition by hydrogen-bond-surrogate α-helices: selective inhibition of the p53/MDM2 complex.

Authors:  Laura K Henchey; Jason R Porter; Indraneel Ghosh; Paramjit S Arora
Journal:  Chembiochem       Date:  2010-10-18       Impact factor: 3.164

9.  A Facile N-Mercaptoethoxyglycinamide (MEGA) Linker Approach to Peptide Thioesterification and Cyclization.

Authors:  Patrick M M Shelton; Caroline E Weller; Champak Chatterjee
Journal:  J Am Chem Soc       Date:  2017-03-09       Impact factor: 15.419

Review 10.  Protein Domain Mimics as Modulators of Protein-Protein Interactions.

Authors:  Nicholas Sawyer; Andrew M Watkins; Paramjit S Arora
Journal:  Acc Chem Res       Date:  2017-05-31       Impact factor: 22.384
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