Literature DB >> 25277500

Asymmetric catalysis with short-chain peptides.

Bartosz Lewandowski1, Helma Wennemers2.   

Abstract

Within this review article we describe recent developments in asymmetric catalysis with peptides. Numerous peptides have been established in the past two decades that catalyze a wide variety of transformations with high stereoselectivities and yields, as well as broad substrate scope. We highlight here catalytically active peptides, which have addressed challenges that had thus far remained elusive in asymmetric catalysis: enantioselective synthesis of atropoisomers and quaternary stereogenic centers, regioselective transformations of polyfunctional substrates, chemoselective transformations, catalysis in-flow and reactions in aqueous environments.
Copyright © 2014 Elsevier Ltd. All rights reserved.

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Year:  2014        PMID: 25277500     DOI: 10.1016/j.cbpa.2014.09.011

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  13 in total

1.  Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3-Arylquinazolin-4(3H)-ones.

Authors:  Jennifer M Crawford; Elizabeth A Stone; Anthony J Metrano; Scott J Miller; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

2.  Convenient synthesis of collagen-related tripeptides for segment condensation.

Authors:  Aubrey J Ellison; Brett VanVeller; Ronald T Raines
Journal:  Biopolymers       Date:  2015-11       Impact factor: 2.505

3.  Site-Selective Cysteine-Cyclooctyne Conjugation.

Authors:  Chi Zhang; Peng Dai; Alexander A Vinogradov; Zachary P Gates; Bradley L Pentelute
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-26       Impact factor: 15.336

4.  Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination.

Authors:  A J Metrano; N C Abascal; B Q Mercado; E K Paulson; S J Miller
Journal:  Chem Commun (Camb)       Date:  2016-03-10       Impact factor: 6.222

5.  Isolating Conformers to Assess Dynamics of Peptidic Catalysts Using Computationally Designed Macrocyclic Peptides.

Authors:  Elizabeth A Stone; Parisa Hosseinzadeh; Timothy W Craven; Michael J Robertson; Yaodong Han; Sheng-Ying Hsieh; Anthony J Metrano; David Baker; Scott J Miller
Journal:  ACS Catal       Date:  2021-03-25       Impact factor: 13.084

Review 6.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

7.  Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.

Authors:  Xin Cindy Yan; Anthony J Metrano; Michael J Robertson; Nadia C Abascal; Julian Tirado-Rives; Scott J Miller; William L Jorgensen
Journal:  ACS Catal       Date:  2018-09-13       Impact factor: 13.084

8.  Diversity of Secondary Structure in Catalytic Peptides with β-Turn-Biased Sequences.

Authors:  Anthony J Metrano; Nadia C Abascal; Brandon Q Mercado; Eric K Paulson; Anna E Hurtley; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-12-28       Impact factor: 15.419

9.  Importance of dipole moments and ambient polarity for the conformation of Xaa-Pro moieties - a combined experimental and theoretical study.

Authors:  Christiane Siebler; Boris Maryasin; Michael Kuemin; Roman S Erdmann; Carla Rigling; Claudio Grünenfelder; Christian Ochsenfeld; Helma Wennemers
Journal:  Chem Sci       Date:  2015-08-12       Impact factor: 9.825

10.  Design and Synthesis of Helical N-Terminal L-Prolyl Oligopeptides Possessing Hydrocarbon Stapling.

Authors:  Atsushi Ueda; Mei Higuchi; Kazuki Sato; Tomohiro Umeno; Masakazu Tanaka
Journal:  Molecules       Date:  2020-10-13       Impact factor: 4.411

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