Literature DB >> 18407642

Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether.

Kengo Akagawa1, Hajime Akabane, Seiji Sakamoto, Kazuaki Kudo.   

Abstract

A resin-supported N-terminal prolyl peptide having a beta-turn motif and hydrophobic polyleucine chain effectively catalyzed the asymmetric transfer hydrogenation under aqueous conditions. The polyleucine tether provides a hydrophobic cavity in aqueous media that brought about a remarkable acceleration of the reaction. In addition, the polyleucine chain also turned out to be essential for high enantioselectivity.

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Year:  2008        PMID: 18407642     DOI: 10.1021/ol800031p

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


  8 in total

Review 1.  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

2.  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

3.  Asymmetric one-pot sequential Friedel-Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme.

Authors:  Kengo Akagawa; Ryota Umezawa; Kazuaki Kudo
Journal:  Beilstein J Org Chem       Date:  2012-08-17       Impact factor: 2.883

4.  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

5.  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

6.  Development of fructose-1,6-bisphosphate aldolase enzyme peptide mimics as biocatalysts in direct asymmetric aldol reactions.

Authors:  Thabo Peme; Dean Brady; Wanyama Juma; Maya Makatini
Journal:  RSC Adv       Date:  2021-11-15       Impact factor: 4.036

7.  Stereoselective peptide catalysis in complex environments - from river water to cell lysates.

Authors:  Tobias Schnitzer; Jonas W Rackl; Helma Wennemers
Journal:  Chem Sci       Date:  2022-06-14       Impact factor: 9.969

8.  Experimental lineage and functional analysis of a remotely directed peptide epoxidation catalyst.

Authors:  Phillip A Lichtor; Scott J Miller
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

  8 in total

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