scholarly journals Metalloporphyrin Dimers Bridged by a Peptoid Helix: Host-Guest Interaction and Chiral Recognition

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2741 ◽  
Author(s):  
Yen Lee ◽  
Boyeong Kang ◽  
Jiwon Seo

Co-facial porphyrins have been designed to construct porphyrin tweezers with versatile molecular recognition capabilities. In this study, we synthesized metalloporphyrin–peptoid conjugates (MPPCs) displaying two metalloporphyrins on a peptoid scaffold with either achiral unfolded (1) or helical (2 and 3) secondary structures. Host–guest complexation of MPPCs was realized with various guests of different lengths and basicities, and the extent of complexation was measured by UV-vis and circular dichroism (CD) spectroscopic titration. Intermolecular and intramolecular chirality induction were observed on achiral and chiral peptoid backbones, respectively. Spectroscopic data indicated that a broad scope of achiral guests can be recognized by chiral 2; in particular, longer and more flexible guests were seen to bind more tightly on 2. In addition, chiral 2 provided a distinct CD couplet with dl-, d-, or l-Lys-OMe, which was a result of the diastereomeric host–guest complex formation. Our results indicated that MPPCs can recognize, contrast, and analyze various achiral, chiral, or racemic molecules. Based on co-facial metalloporphyrins present on peptoid scaffolds, we developed a novel class of porphyrin tweezers, which can be further utilized in asymmetric catalysis, molecular sensing, and drug delivery.

2021 ◽  
Vol 154 (15) ◽  
pp. 154105
Author(s):  
Zahra Shadfar ◽  
Oussama Yahiaoui ◽  
Thomas A. Collier ◽  
Thomas Fallon ◽  
Jane R. Allison

2017 ◽  
Vol 53 (13) ◽  
pp. 2126-2129 ◽  
Author(s):  
Marc Padilla ◽  
Francesca Peccati ◽  
José Luis Bourdelande ◽  
Xavier Solans-Monfort ◽  
Gonzalo Guirado ◽  
...  

Gold nanoparticles coated with cyclodextrins show enhanced plasmon-based photocatalytic activities by promoting catalyst–reactant approximationviasupramolecular host–guest complex formation.


2012 ◽  
Vol 554-556 ◽  
pp. 27-30
Author(s):  
Hui Xie ◽  
Yan Min Wang

The supramolecular interaction of BPO and ß-CD has been studied by spectrophtometry. The mechanism of the inclusion was studied. The results showed that ß-CD react with BPO to form a 2:1 or 1:1 host-guest complex.The ß-CD reacts with benzoic acid to form a 1:1 host-guest complex after the BPO was reduced by hydroxyl ammonium chloride.Based on the enhancement of the absorbance of BPO produced through complex formation, a spectrophotometric method for determination BPO in bulk aqueous solution in the presence of ß-CD was developed. A linear relationship between the absorbance and BPO concentration was obtained in the range of 0.2~50 μg.ml-1. The proposed method was used to determine the BPO in the flour with satisfactory results. The principal advantage of the proposed method is its excellent selectivity based on molecule recognition of ß-CD and simple.


2017 ◽  
Vol 53 (10) ◽  
pp. 1688-1691 ◽  
Author(s):  
Peifa Wei ◽  
Haoze Wang ◽  
Kecheng Jie ◽  
Feihe Huang

We design a coumarin-containing bis(m-phenylene)-32-crown-10 derivative which efficiently controls the regio- and stereo-selectivity of the photodimerization of its two terminal coumarin groups templated by taco-type host–guest complex formation to selectively produce the syn-head-to-tail cryptand isomer in quantitative yield.


2020 ◽  
Vol 26 (72) ◽  
pp. 17288-17288
Author(s):  
Timo Schillmöller ◽  
Paul Niklas Ruth ◽  
Regine Herbst‐Irmer ◽  
Dietmar Stalke

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