molecules-logo

Journal Browser

Journal Browser

Organocatalysis II: Bioinspired and Supramolecular Catalysts

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 February 2021) | Viewed by 5776

Special Issue Editor


E-Mail Website
Guest Editor
Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), c/Jordi Girona 18-26, E08034 Barcelona, Spain
Interests: asymmetric catalysis; organocatalysis; supramolecular catalysis; bioinspired catalysis

Special Issue Information

Dear Colleagues,

Today, organocatalysis is a mature field that nonetheless continues to expand and introduce novel concepts to organic chemistry. Along with metal catalysis and biocatalysis, organocatalysis constitutes one of the pillars of modern asymmetric catalysis. Its future evolution can be envisaged to be pointing towards two intercrossing, interdependent directions: the discovery of new organocatalytic reactions and the search for novel catalytic structures. Although it is often impossible to separate one direction from the other, we want to emphasize in this Special Issue the latest organocatalysts that have been developed. In this respect, we will focus on bioinspired organocatalysts, which include structures such as small peptides and natural product-based catalysts as well as asymmetric catalysts inspired by the mode of action of enzymes. We would like to include supramolecular organocatalysts in this Special Issue as well, because weak interactions such as hydrophobic, pi–pi, or hydrogen bonding are ubiquitous in both biological catalysts and organocatalysts, determining the catalyst–substrate structure and the subsequent mechanistic scenario. Bioinspired and supramolecular organocatalysts are, therefore, strongly interrelated. Authors are encouraged to submit their research on this topic in the form of communications, research articles, or focused reviews. Those considering the submission of a review are kindly asked to contact the Guest Editor in advance to provide a brief outline of the subject to avoid overlapping.

Dr. Ciril Jimeno
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Organocatalysis
  • Bioinspired catalysis
  • Supramolecular catalysis
  • Catalytic peptides

Published Papers (2 papers)

Order results
Result details
Select all
Export citation of selected articles as:

Research

8 pages, 2254 KiB  
Communication
Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction
by Ciril Jimeno
Molecules 2021, 26(4), 826; https://doi.org/10.3390/molecules26040826 - 5 Feb 2021
Cited by 5 | Viewed by 2276
Abstract
The binding and stabilizing effect of arginine residues in certain aldolases served as inspiring source for the development of a family of amino acylguanidine organocatalysts. Screening and optimization led to identify the threonine derivative as the most suitable catalyst for the asymmetric aldol [...] Read more.
The binding and stabilizing effect of arginine residues in certain aldolases served as inspiring source for the development of a family of amino acylguanidine organocatalysts. Screening and optimization led to identify the threonine derivative as the most suitable catalyst for the asymmetric aldol addition of hydroxyacetone, affording the syn diastereomer in high ee. In contrast, the proline derivative yielded the anti diasteromer. MMFF models suggest the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates. Full article
(This article belongs to the Special Issue Organocatalysis II: Bioinspired and Supramolecular Catalysts)
Show Figures

Graphical abstract

15 pages, 1733 KiB  
Article
Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis
by Aitor Arlegui, Pol Torres, Victor Cuesta, Joaquim Crusats and Albert Moyano
Molecules 2020, 25(15), 3420; https://doi.org/10.3390/molecules25153420 - 28 Jul 2020
Cited by 6 | Viewed by 3035
Abstract
Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the [...] Read more.
Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the hybrid leads to the formation of self-assembled structures, so that the hybrids flocculate and their catalytic activity is fully suppressed. The low degree of chirality transfer observed for aqueous Michael and aldol reactions strongly suggests that these reactions take place under true “in water” organocatalytic conditions. The highly insoluble catalyst aggregates can easily be separated from the reaction products by centrifugation of the acidic reaction mixtures, and after neutralization and desalting, the sodium salts of the sulfonated amine-porphyrin hybrids, retaining their full catalytic activity, can be recovered in high yield. Full article
(This article belongs to the Special Issue Organocatalysis II: Bioinspired and Supramolecular Catalysts)
Show Figures

Graphical abstract

Back to TopTop