Chiral Recognition Via a Stereodynamic Vanadium Probe Using ECD-ROA Interference

Author(s):  
Ewa Machalska ◽  
Natalia Hachlica ◽  
Grzegorz Zajac ◽  
Davide Carraro ◽  
Malgorzata Baranska ◽  
...  

Intermolecular interactions sensitive to chirality occur in many biological events. We report a complex formation between a versatile vanadium-based probe and a chiral co-ligand monitored through the interference of electronic...

1994 ◽  
Vol 43 (10) ◽  
pp. 769-778
Author(s):  
Hisanobu OGOSHI ◽  
Tadashi EMA ◽  
Tadashi MIZUTANI

1994 ◽  
Vol 43 (12) ◽  
pp. 2122-2125 ◽  
Author(s):  
N. O. Cherskaya ◽  
O. V. Kharitonova ◽  
V. A. Shlyapochnikov ◽  
T. S. Novikova ◽  
L. I. Khmel'nitskii

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.


Symmetry ◽  
2020 ◽  
Vol 12 (5) ◽  
pp. 758 ◽  
Author(s):  
Zita Rádai ◽  
Péter Bagi ◽  
Mátyás Czugler ◽  
Konstantin Karaghiosoff ◽  
György Keglevich

Two dimethyl α-hydroxy-arylmethylphosphonates (aryl = Ph and 2-MeOPh) were subjected to optical resolution via diastereomer complex formation applying the acidic calcium salt of O,O′-dibenzoyl-(2R,3R)-tartaric acid as the resolving agent. The dominating diastereomer complexes, whose structure was determined by single crystal X-ray measurements, were obtained in 96% and 68% diastereomer excess values, respectively. After decomposing the diastereomer formations by extraction, and after recrystallizations, the major enantiomer (S and R, respectively) of the α-hydroxyphosphonates were prepared in enantiomeric excess values of 96% and 68%, respectively. The stereostructure of the two α-hydroxy-arylmethylphosphonates was again established by X-ray measurements. Detailed study on the X-ray data allowed valuable conclusions on the nature of the coordination in the complexes (intermolecular interactions), and on the H-bonding.


2021 ◽  
Vol 23 (38) ◽  
pp. 21489-21495
Author(s):  
Mykola Telychko ◽  
Lulu Wang ◽  
Chia-Hsiu Hsu ◽  
Guangwu Li ◽  
Xinnan Peng ◽  
...  

Long-range chiral recognition patterns in supramolecular assemblies were tailored by engineering the weak non-covalent intermolecular interactions.


2018 ◽  
Vol 54 (81) ◽  
pp. 11407-11410 ◽  
Author(s):  
Diksha Gambhir ◽  
Sunil Kumar ◽  
Gourab Dey ◽  
Venkata Krishnan ◽  
Rik Rani Koner

Enantioselective recognition of chiral amines through gel formation and collapse.


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