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Literature DB >> 27529332

Cell-Permeable Peptides Containing Cycloalanine Residues.

Hao Wu¹, Guillaume Mousseau², Sonia Mediouni², Susana T Valente², Thomas Kodadek³.

Abstract

We present here an efficient alternative to N-methylation for the purpose of morphing protein-binding peptides into more serum-stable and cell-permeable compounds. This involves the incorporation of a cycloalanine (CyAla) into a peptide in a way that avoids difficult coupling steps. We demonstrate the utility of this chemistry in creating a cell-permeable derivative of a high-affinity HIV Rev protein-binding peptide.

Entities: CellLine Chemical Disease Gene Species

Keywords: HIV Rev; antiviral; cell permeability; cyclic peptides; peptidomimetics

Mesh：

Substances：

Year: 2016 PMID： 27529332 PMCID： PMC5220248 DOI： 10.1002/anie.201605745

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

26 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. An analog of the natural steroidal alkaloid cortistatin A potently suppresses Tat-dependent HIV transcription.

Authors: Guillaume Mousseau; Mark A Clementz; Wendy N Bakeman; Nisha Nagarsheth; Michael Cameron; Jun Shi; Phil Baran; Rémi Fromentin; Nicolas Chomont; Susana T Valente
Journal: Cell Host Microbe Date: 2012-07-19 Impact factor: 21.023

3. The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides.

Authors: Oded Ovadia; Sarit Greenberg; Jayanta Chatterjee; Burkhardt Laufer; Florian Opperer; Horst Kessler; Chaim Gilon; Amnon Hoffman
Journal: Mol Pharm Date: 2011-03-21 Impact factor: 4.939

4. Solid-phase synthesis of diverse peptide tertiary amides by reductive amination.

Authors: Kevin Pels; Thomas Kodadek
Journal: ACS Comb Sci Date: 2015-02-25 Impact factor: 3.784

5. Solid-phase synthesis and characterization of N-methyl-rich peptides.

Authors: M Teixidó; F Albericio; E Giralt
Journal: J Pept Res Date: 2005-02

6. Generation and characterization of a chimeric rabbit/human Fab for co-crystallization of HIV-1 Rev.

Authors: Stephen J Stahl; Norman R Watts; Christoph Rader; Michael A DiMattia; Rose G Mage; Ira Palmer; Joshua D Kaufman; Jonathan M Grimes; David I Stuart; Alasdair C Steven; Paul T Wingfield
Journal: J Mol Biol Date: 2010-02-04 Impact factor: 5.469

7. KPT-330 inhibitor of CRM1 (XPO1)-mediated nuclear export has selective anti-leukaemic activity in preclinical models of T-cell acute lymphoblastic leukaemia and acute myeloid leukaemia.

Authors: Julia Etchin; Takaomi Sanda; Marc R Mansour; Alex Kentsis; Joan Montero; Bonnie T Le; Amanda L Christie; Dilara McCauley; Scott J Rodig; Michael Kauffman; Sharon Shacham; Richard Stone; Anthony Letai; Andrew L Kung; A Thomas Look
Journal: Br J Haematol Date: 2013-02-04 Impact factor: 6.998

5. MOrPH-PhD: An Integrated Phage Display Platform for the Discovery of Functional Genetically Encoded Peptide Macrocycles.

Authors: Andrew E Owens; Jacob A Iannuzzelli; Yu Gu; Rudi Fasan
Journal: ACS Cent Sci Date: 2020-02-04 Impact factor: 14.553

6. Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells.

Authors: Jacob A Iannuzzelli; Rudi Fasan
Journal: Chem Sci Date: 2020-05-27 Impact factor: 9.825

6 in total

Cell-Permeable Peptides Containing Cycloalanine Residues.

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

2. An analog of the natural steroidal alkaloid cortistatin A potently suppresses Tat-dependent HIV transcription.

3. The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides.

4. Solid-phase synthesis of diverse peptide tertiary amides by reductive amination.

5. Solid-phase synthesis and characterization of N-methyl-rich peptides.

6. Generation and characterization of a chimeric rabbit/human Fab for co-crystallization of HIV-1 Rev.

7. KPT-330 inhibitor of CRM1 (XPO1)-mediated nuclear export has selective anti-leukaemic activity in preclinical models of T-cell acute lymphoblastic leukaemia and acute myeloid leukaemia.

8. N-methylation of peptides: a new perspective in medicinal chemistry.

9. DNA-Encoded Solid-Phase Synthesis: Encoding Language Design and Complex Oligomer Library Synthesis.

10. The Tat Inhibitor Didehydro-Cortistatin A Prevents HIV-1 Reactivation from Latency.

1. Post-Translational Backbone Engineering through Selenomethionine-Mediated Incorporation of Freidinger Lactams.

2. Understanding Cell Penetration of Cyclic Peptides.

3. Tuning conformation and properties of peptidomimetic backbones through dual N/C_α-substitution.

Review 4. Emerging Methods and Design Principles for Cell-Penetrant Peptides.

5. MOrPH-PhD: An Integrated Phage Display Platform for the Discovery of Functional Genetically Encoded Peptide Macrocycles.

6. Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells.