Vibrational circular dichroism study of optically pure cryptophane-A

Journal of the American Chemical Society
Thierry BrotinThierry Buffeteau

Abstract

Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the absolute configuration of optically pure cryptophane-A molecule. This large molecule (120 atoms) that possess a globular shape, but no chiral centers, exceeds the molecular size of published structures for which VCD has been used to determine the absolute configuration. VCD spectra recorded in CDCl(3) solution for the two resolved enantiomers are near mirror images, and very good agreement between the observed IR and VCD spectra and intensity calculations performed at the DFT (B3PW91/6-31G) level establish, besides the absolute configuration, the preferential anti conformation of the aliphatic linkers of the chloroform-cryptophane-A complex. Experiments performed in CD(2)Cl(2) and C(2)D(2)Cl(4) solutions show no significant modifications in the IR and VCD spectra, indicating that the conformation of the aliphatic linkers is similar for empty (C(2)D(2)Cl(4) solution) and encaged (CDCl(3) and CD(2)Cl(2) solutions) cryptophane-A molecules.

Citations

Jan 27, 2011·Nature Communications·Olena TaratulaIvan J Dmochowski
Nov 19, 2008·Physical Chemistry Chemical Physics : PCCP·Guochun Yang, Yunjie Xu
Jun 24, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Guochun YangYufen Zhao
Jan 14, 2016·Journal of Chemical Theory and Computation·K V Jovan Jose, Krishnan Raghavachari
Nov 18, 2015·Journal of Chemical Theory and Computation·K V Jovan JoseKrishnan Raghavachari
Jun 20, 2015·The Journal of Physical Chemistry. B·Thierry BrotinThierry Buffeteau
Jul 1, 2010·Magnetic Resonance in Chemistry : MRC·Z TakacsJ P Dutasta
Nov 8, 2012·Magnetic Resonance in Chemistry : MRC·Z TakacsJ-P Dutasta
Feb 16, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Peiyang ZhuYunjie Xu
May 1, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mohammad Reza PoopariYunjie Xu
Jun 4, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Corina H PollokChristian Merten
Feb 10, 2017·The Journal of Chemical Physics·Kevin ReiterFlorian Weigend
May 28, 2019·Chirality·Orsola BaydounThierry Brotin
Dec 7, 2007·The Journal of Organic Chemistry·Dominique CavagnatThierry Brotin
Dec 18, 2008·Chemical Reviews·Thierry Brotin, Jean-Pierre Dutasta
May 18, 2007·The Journal of Physical Chemistry. a·Laurent DucasseThierry Buffeteau
Oct 22, 2008·The Journal of Organic Chemistry·Atsuya MuranakaNagao Kobayashi
Aug 20, 2008·The Journal of Physical Chemistry. a·Thierry BrotinThierry Buffeteau
Jun 12, 2021·Physical Chemistry Chemical Physics : PCCP·Luisa Weirich, Christian Merten
Dec 24, 2011·The Journal of Organic Chemistry·Thierry BrotinThierry Buffeteau
Feb 12, 2011·Journal of the American Chemical Society·Nadeau ChristianKevin Belyk
Aug 4, 2012·The Journal of Physical Chemistry. B·Thierry BrotinThierry Buffeteau
Feb 4, 2012·Journal of the American Chemical Society·Tohru Taniguchi, Kenji Monde
Apr 29, 2014·The Journal of Physical Chemistry. B·Nicolas DaugeyThierry Buffeteau
Jun 14, 2012·The Journal of Physical Chemistry. B·Zoltan TakacsJozef Kowalewski
Jan 28, 2011·The Journal of Organic Chemistry·Aude BouchetThierry Buffeteau
Dec 16, 2016·The Journal of Physical Chemistry. B·Delphine PitratThierry Brotin
Apr 8, 2011·The Journal of Organic Chemistry·Aude BouchetThierry Buffeteau
Jan 30, 2014·The Journal of Physical Chemistry. B·Z TakacsT Brotin

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.