Effective Enantioselective Recognition by Chiral Amino-Phosphonium Salts*.

Angewandte Chemie
Prabhakaran RajasekarRamamoorthy Boomishankar

Abstract

The research on chiral recognition and selection is not only fundamental in deciding the mystery of homochirality, but also informative in terms of substrate recognition in biological processes and asymmetric catalysis. We report an enantiomeric pair of phosphonium salts having chiral (R and S) amino substituents that are utilized towards the enantioselective recognition of a variety of chiral compounds having functional groups, such as carboxylic acid, amine, and alcohol. These simple phosphonium salts are found to exhibit a high enantiomeric discrimination for 1-cyclohexylethylamine (CY). A remarkable guest selectivity (ξ) value of 5.3×108 is achieved for the enantiomer of R-CY over S-CY by using the R-isomer of the phosphonium salt. Such high binding selectivities and discrimination capabilities is attributed to multiple non-covalent interactions between the host and guest molecules as inferred from the DFT optimized structures of the host-guest pairs.

References

Apr 1, 1991·Biochemical Society Transactions·A H Beckett
Mar 27, 2001·Accounts of Chemical Research·R Warmuth, J Yoon
Feb 19, 2002·Chemical Reviews·Ronald Breslow, Steven D. Dong
Feb 19, 2002·Chemical Reviews·Ayub Jasat, John C. Sherman
May 13, 2004·Chemical Reviews·George W GokelMichelle E Weber
Jul 30, 2005·Angewandte Chemie·Jason LagonaLyle Isaacs
Dec 22, 2007·Chemical Reviews·Guy A HemburyYoshihisa Inoue
Dec 18, 2008·Chemical Reviews·Thierry Brotin, Jean-Pierre Dutasta
May 3, 2002·Angewandte Chemie·Fraser HofJulius Rebek
Oct 12, 2010·Journal of Computational Chemistry·Neetha MohanCherumuttathu H Suresh
Oct 28, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Michael MüllerKari Rissanen
Sep 18, 2012·Chemical Communications : Chem Comm·Mohit KumarSubi J George
Feb 23, 2013·Journal of the American Chemical Society·Toshiyuki KidaMitsuru Akashi
Aug 31, 2013·Science·Hiroyasu FurukawaOmar M Yaghi
Sep 10, 2013·Chemistry : a European Journal·Johannes AmmerHerbert Mayr
Dec 18, 2013·Chemical Society Reviews·Gang Zhang, Michael Mastalerz
Jun 19, 2014·Chemical Society Reviews·Kenji Kobayashi, Masamichi Yamanaka
Sep 24, 2014·Chemical Reviews·Grégorio Crini
Mar 5, 2015·Chemical Society Reviews·Simon E Lewis
Mar 4, 2017·Science·Christian S Diercks, Omar M Yaghi
May 4, 2017·Chemical Society Reviews·Zhichang LiuJ Fraser Stoddart
May 10, 2017·Angewandte Chemie·Stephen D P FieldenSteffen L Woltering
Jun 21, 2017·Angewandte Chemie·Jean-Pierre Sauvage
Aug 19, 2017·Faraday Discussions·Bunyarat RungtaweevoranitOmar M Yaghi

❮ Previous
Next ❯

Citations

Aug 4, 2021·ACS Applied Materials & Interfaces·Zhen-Zhang WengLan-Sun Zheng

❮ Previous
Next ❯

Related Concepts

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.