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Host-Guest Chemistry
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Host-Guest Chemistry

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

Deadline for manuscript submissions: closed (15 July 2015) | Viewed by 25854

Special Issue Editor

Dr. David B. Smithrud

E-Mail Website
Guest Editor
Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221, USA
Interests: molecular recognition; cell transport; DNA binding agents; peptidomimetics; host-guest chemistry; catalysis; synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In life, noncovalent complexation precludes the formation of covalent bonds and is a crucial step in signaling events. Chemists have spent many years constructing covalently linked hosts to replicate the noncovalent complexes observed in nature. The first generation of hosts formed strong noncovalent bonds with a guest through rigid pockets that matched a guest’s size. Although able to form tight complexes with some selectivity, these hosts did not achieve the very large association constants observed in nature and lacked function. The scope of this Special Issue highlights the newest approaches in constructing hosts to maximize guest association and perform function through dynamic motion.

Dr. David B. Smithrud
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

  • host-guest
  • molecular recognition
  • sensors
  • biomimetics
  • protein mimetics

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Published Papers (4 papers)

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Research

8 pages, 1044 KiB  
Article
A Versatile Axle for the Construction of Disassemblage Rotaxanes
by Lucas A. Powers and David B. Smithrud
Molecules 2016, 21(8), 1043; https://doi.org/10.3390/molecules21081043 - 10 Aug 2016
Cited by 3 | Viewed by 3692
Abstract
Rotaxanes are unique mechanical devices that hold great promise as sensors. We report on two new rotaxanes that contain an acid or base sensitive trigger and readily disassemble in a wide range of environments. Disassemblage was observed under TLC and 1H-NMR analysis. [...] Read more.
Rotaxanes are unique mechanical devices that hold great promise as sensors. We report on two new rotaxanes that contain an acid or base sensitive trigger and readily disassemble in a wide range of environments. Disassemblage was observed under TLC and 1H-NMR analysis. The axle is highly charged, which enhances solubility in aqueous environments, and can be readily derivatized with sensor components. The trigger was swapped in a one-pot method, which is promising for the rapid production of a series of sensors. Full article
(This article belongs to the Special Issue Host-Guest Chemistry)
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13 pages, 1027 KiB  
Article
The Effect of Number and Position of P=O/P=S Bridging Units on Cavitand Selectivity toward Methyl Ammonium Salts
by Daniela Menozzi, Roberta Pinalli, Chiara Massera, Francesca Maffei and Enrico Dalcanale
Molecules 2015, 20(3), 4460-4472; https://doi.org/10.3390/molecules20034460 - 10 Mar 2015
Cited by 4 | Viewed by 5268
Abstract
The present work reports the synthesis and complexation properties of five mixed bridge P=O/P=S cavitands toward N,N-methyl butyl ammonium chloride (1) as prototype guest. The influence of number and position of P=O and P=S groups on the affinity of phosphonate [...] Read more.
The present work reports the synthesis and complexation properties of five mixed bridge P=O/P=S cavitands toward N,N-methyl butyl ammonium chloride (1) as prototype guest. The influence of number and position of P=O and P=S groups on the affinity of phosphonate cavitands toward 1 is assessed via ITC titrations in DCE as solvent. Comparison of the resulting Kass values, the enthalpic and entropic contributions to the overall binding with those of the parent tetraphosphonate Tiiii and tetrathiophosphonate TSiiii cavitands allows one to single out the simultaneous dual H-bond between the cavitand and the salt as the major player in complexation. Full article
(This article belongs to the Special Issue Host-Guest Chemistry)
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17 pages, 2646 KiB  
Article
Investigation of Structural Mimetics of Natural Phosphate Ion Binding Motifs
by Evgeny A. Kataev and Tatiana A. Shumilova
Molecules 2015, 20(2), 3354-3370; https://doi.org/10.3390/molecules20023354 - 16 Feb 2015
Cited by 8 | Viewed by 7518
Abstract
Phosphates are ubiquitous in biology and nearly half of all proteins interact with their partners by means of recognition of phosphate residues. Therefore, a better understanding of the phosphate ion binding by peptidic structures is highly desirable. Two new receptors have been designed [...] Read more.
Phosphates are ubiquitous in biology and nearly half of all proteins interact with their partners by means of recognition of phosphate residues. Therefore, a better understanding of the phosphate ion binding by peptidic structures is highly desirable. Two new receptors have been designed and synthesized and their anion binding properties in an acetonitrile solution have been determined. The structure of hosts mimics a part of the kinase active site that is responsible for the recognition of the phosphate residue. New hosts contain additional free amino groups with the aim to facilitate coordination of protonated anions, such as dihydrogen phosphate. According to spectrophotometric measurements, stepwise 1:1 and 1:2 binding modes have been observed for both receptors in the presence of acetate, hydrogen sulfate and dihydrogen phosphate. Compared with the acyclic receptor, the macrocyclic receptor has demonstrated a remarkably enhanced selectivity for dihydrogen phosphate over other anions. Fluorometric measurements have revealed different responses of the acyclic and macrocyclic receptors towards anions. However, in both cases, a 5–8 nm hypsochromic shift of fluorescence maximum has been observed upon interaction of acetate and dihydrogen phosphate with receptors. Full article
(This article belongs to the Special Issue Host-Guest Chemistry)
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13 pages, 1598 KiB  
Article
A Redox-Controllable Molecular Switch Based on Weak Recognition of BPX26C6 at a Diphenylurea Station
by Jia-Cheng Chang, Chien-Chen Lai and Sheng-Hsien Chiu
Molecules 2015, 20(2), 1775-1787; https://doi.org/10.3390/molecules20021775 - 22 Jan 2015
Cited by 2 | Viewed by 8458
Abstract
The Na+ ion–assisted recognition of urea derivatives by BPX26C6 has allowed the construction of a redox-controllable [2]rotaxane-type molecular switch based on two originally very weakly interacting host/guest systems. Using NOBF4 to oxidize the triarylamine terminus into a corresponding radical cation attracted [...] Read more.
The Na+ ion–assisted recognition of urea derivatives by BPX26C6 has allowed the construction of a redox-controllable [2]rotaxane-type molecular switch based on two originally very weakly interacting host/guest systems. Using NOBF4 to oxidize the triarylamine terminus into a corresponding radical cation attracted the macrocyclic component toward its adjacent carbamate station; subsequent addition of Zn powder moved the macrocyclic component back to its urea station. Full article
(This article belongs to the Special Issue Host-Guest Chemistry)
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