Literature DB >> 17020289

Trisubstituted (E)-alkene dipeptide isosteres as beta-turn promoters in the gramicidin S cyclodecapeptide scaffold.

Jingbo Xiao1, Bernard Weisblum, Peter Wipf.   

Abstract

[reaction: see text] A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both d-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and successfully mimic a proline residue.

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Year:  2006        PMID： 17020289      PMCID： PMC2631548          DOI： 10.1021/ol0617704

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


  26 in total

1.  Methyl- and (Trifluoromethyl)alkene Peptide Isosteres: Synthesis and Evaluation of Their Potential as beta-Turn Promoters and Peptide Mimetics.

Authors:  Peter Wipf; Todd C. Henninger; Steven J. Geib
Journal:  J Org Chem       Date:  1998-09-04       Impact factor: 4.354

2.  Three-component aldimine addition--cyclopropanation. an efficient new methodology for amino cyclopropane synthesis.

Authors:  P Wipf; C Kendall; C R Stephenson
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

3.  Beta-turn modified gramicidin S analogues containing arylated sugar amino acids display antimicrobial and hemolytic activity comparable to the natural product.

Authors:  Gijsbert M Grotenbreg; Annelies E M Buizert; Antonio L Llamas-Saiz; Emile Spalburg; Peter A V van Hooft; Albert J de Neeling; Daan Noort; Mark J van Raaij; Gijsbert A van der Marel; Herman S Overkleeft; Mark Overhand
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

Review 4.  Peptide, peptidomimetic and small-molecule drug discovery targeting HIV-1 host-cell attachment and entry through gp120, gp41, CCR5 and CXCR4.

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Authors:  Noah Levinson; Rochelle Hinman; Ashwini Patil; Corey R J Stephenson; Stefan Werner; Grace H C Woo; Jingbo Xiao; Peter Wipf; Kristen W Lynch
Journal:  RNA       Date:  2006-03-23       Impact factor: 4.942

6.  Electrostatic versus steric effects in peptidomimicry: synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres.

Authors:  Jingbo Xiao; Bernard Weisblum; Peter Wipf
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

7.  The influence of peptide structure on transport across Caco-2 cells. II. Peptide bond modification which results in improved permeability.

Authors:  R A Conradi; A R Hilgers; N F Ho; P S Burton
Journal:  Pharm Res       Date:  1992-03       Impact factor: 4.200

8.  Synthesis of Sulfur-Containing Olefinic Peptide Mimetic Farnesyl Transferase Inhibitors Using the Nozaki-Hiyama-Kishi Reaction and Cuprate S(N)2' Displacements.

Authors:  Hu Yang; Xiaoning C. Sheng; Edmund M. Harrington; Karen Ackermann; Ana Maria Garcia; Michael D. Lewis
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Journal:  J Med Chem       Date:  2003-04-24       Impact factor: 7.446

10.  Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements.

Authors:  Xiaodong J Wang; Scott A Hart; Bailing Xu; Matthew D Mason; John R Goodell; Felicia A Etzkorn
Journal:  J Org Chem       Date:  2003-03-21       Impact factor: 4.354
View more
  10 in total

1.  Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents.

Authors:  Peter Wipf; Jingbo Xiao; Corey R J Stephenson
Journal:  Chimia (Aarau)       Date:  2009-11       Impact factor: 1.509

2.  Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

Authors:  Marie-Céline Frantz; Joshua G Pierce; Joan M Pierce; Li Kangying; Wan Qingwei; Matthew Johnson; Peter Wipf
Journal:  Org Lett       Date:  2011-03-31       Impact factor: 6.005

3.  Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres.

Authors:  Erin M Skoda; Gary C Davis; Peter Wipf
Journal:  Org Process Res Dev       Date:  2012       Impact factor: 3.317

4.  Synthesis of analogs of the radiation mitigator JP4-039 and visualization of BODIPY derivatives in mitochondria.

Authors:  Marie-Céline Frantz; Erin M Skoda; Joshua R Sacher; Michael W Epperly; Julie P Goff; Joel S Greenberger; Peter Wipf
Journal:  Org Biomol Chem       Date:  2013-07-07       Impact factor: 3.876

5.  Therapeutic index of gramicidin S is strongly modulated by D-phenylalanine analogues at the beta-turn.

Authors:  Concepción Solanas; Beatriz G de la Torre; María Fernández-Reyes; Clara M Santiveri; M Angeles Jiménez; Luis Rivas; Ana I Jiménez; David Andreu; Carlos Cativiela
Journal:  J Med Chem       Date:  2009-02-12       Impact factor: 7.446

6.  Synthesis and Evaluation of a Mitochondria-Targeting Poly(ADP-ribose) Polymerase-1 Inhibitor.

Authors:  Tanja Krainz; Andrew M Lamade; Lina Du; Taber S Maskrey; Michael J Calderon; Simon C Watkins; Michael W Epperly; Joel S Greenberger; Hülya Bayır; Peter Wipf; Robert S B Clark
Journal:  ACS Chem Biol       Date:  2018-09-14       Impact factor: 5.100

7.  A Mitochondrial-Targeted Nitroxide Is a Potent Inhibitor of Ferroptosis.

Authors:  Tanja Krainz; Michael M Gaschler; Chaemin Lim; Joshua R Sacher; Brent R Stockwell; Peter Wipf
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8.  Engineering β-sheets employing N-methylated heterochiral amino acids.

Authors:  Dipan Ghosh; Priyanka Lahiri; Hitesh Verma; Somnath Mukherjee; Jayanta Chatterjee
Journal:  Chem Sci       Date:  2016-04-21       Impact factor: 9.825

9.  Localized thermodynamic coupling between hydrogen bonding and microenvironment polarity substantially stabilizes proteins.

Authors:  Jianmin Gao; Daryl A Bosco; Evan T Powers; Jeffery W Kelly
Journal:  Nat Struct Mol Biol       Date:  2009-06-14       Impact factor: 15.369

10.  Protein stabilization by tuning the steric restraint at the reverse turn.

Authors:  Priyanka Lahiri; Hitesh Verma; Ashraya Ravikumar; Jayanta Chatterjee
Journal:  Chem Sci       Date:  2018-04-24       Impact factor: 9.825
  10 in total

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