Literature DB >> 30778816

One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates.

Alexander F de la Torre1,2, Akbar Ali3, Fábio Z Galetto4, Antonio L Braga5, José A C Delgado6, Márcio W Paixão7.   

Abstract

A combined organocatalytic and multicomponent synthetic approach was designed for the preparation of selenium-based peptoids and peptide-peptoid conjugates. This single-step synthetic protocol comprises the organocatalytic asymmetric insertion of phenylselenium in the aldehyde moiety followed by the Ugi four-component reaction which results in obtaining the desired compounds in good-to-moderate yields and with good-to-excellent levels of stereoselectivity.

Entities:  

Keywords:  Multicomponent reactions; Organocatalysis; Peptoids; Selenocysteine; Ugi reaction

Year:  2019        PMID: 30778816     DOI: 10.1007/s11030-019-09923-w

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  42 in total

Review 1.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

2.  Selenopeptide chemistry.

Authors:  Markus Muttenthaler; Paul F Alewood
Journal:  J Pept Sci       Date:  2008-12       Impact factor: 1.905

Review 3.  Threading the needle: getting selenocysteine into proteins.

Authors:  Jesse Donovan; Paul R Copeland
Journal:  Antioxid Redox Signal       Date:  2010-04-01       Impact factor: 8.401

4.  Chiral organoselenium-transition-metal catalysts in asymmetric transformations.

Authors:  Marcelo Godoi; Márcio W Paixão; Antonio L Braga
Journal:  Dalton Trans       Date:  2011-09-08       Impact factor: 4.390

5.  Synthesis of selenocysteine peptides and their oxidation to diselenide-bridged compounds.

Authors:  D Besse; L Moroder
Journal:  J Pept Sci       Date:  1997 Nov-Dec       Impact factor: 1.905

6.  Direct synthesis of sensitive selenocysteine peptides by the Ugi reaction.

Authors:  Muhammad Abbas; Ludger A Wessjohann
Journal:  Org Biomol Chem       Date:  2012-10-31       Impact factor: 3.876

7.  Ephedrine-based diselenide: a promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C-C coupling reactions.

Authors:  Letiére C Soares; Eduardo E Alberto; Ricardo S Schwab; Paulo S Taube; Vanessa Nascimento; Oscar E D Rodrigues; Antonio L Braga
Journal:  Org Biomol Chem       Date:  2012-07-17       Impact factor: 3.876

8.  GPx-Like activity of selenides and selenoxides: experimental evidence for the involvement of hydroxy perhydroxy selenane as the active species.

Authors:  Vanessa Nascimento; Eduardo E Alberto; Daniel W Tondo; Daniel Dambrowski; Michael R Detty; Faruk Nome; Antonio L Braga
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

Review 9.  Synthesis of selenocysteine and its derivatives with an emphasis on selenenylsulfide (-Se-S-) formation.

Authors:  Ludger A Wessjohann; Alex Schneider
Journal:  Chem Biodivers       Date:  2008-03       Impact factor: 2.408

10.  One-pot synthesis of highly functionalized seleno amino acid derivatives.

Authors:  Haixia Liu; Alexander Dömling
Journal:  Chem Biol Drug Des       Date:  2009-09       Impact factor: 2.817

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  3 in total

Review 1.  One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds.

Authors:  Saad Shaaban; Hany M Abd El-Lateef; Mai M Khalaf; Mohamed Gouda; Ibrahim Youssef
Journal:  Polymers (Basel)       Date:  2022-05-29       Impact factor: 4.967

2.  Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction.

Authors:  Vitor A Fernandes; Rafaely N Lima; Yoisel B Broterson; Meire Y Kawamura; Radell Echemendía; Alexander F de la Torre; Marco A B Ferreira; Daniel G Rivera; Marcio W Paixão
Journal:  Chem Sci       Date:  2021-09-16       Impact factor: 9.825

3.  Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration.

Authors:  Muhammad Ashfaq; Muhammad Khalid; Muhammad Nawaz Tahir; Akbar Ali; Muhammad Nadeem Arshad; Abdullah M Asiri
Journal:  ACS Omega       Date:  2022-03-14
  3 in total

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