Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps.

Chemical Science
Nam Jung HeoSung Kuk Kim

Abstract

Two-phenoxy walled calix[4]pyrroles 1 and 2 strapped with small rigid linkers containing pyridine and benzene, respectively, have been synthesized. 1H NMR spectroscopic analyses carried out in CDCl3 revealed that both of receptors 1 and 2 recognize only F- and HCO3 - among various test anions with high preference for HCO3 - (as the tetraethylammonium, TEA+ salt) relative to F- (as the TBA+ salt). The bound HCO3 - anion was completely released out of the receptors upon the addition of F- (as the tetrabutylammonium, TBA+ salt) as a result of significantly enhanced affinities and selectivities of the receptors for F- once converted to the TEAHCO3 complexes. Consequently, relatively stable TEAF complexes of receptors 1 and 2 were formed via anion metathesis occurring within the receptor cavities. By contrast, the direct addition of TEAF to receptors 1 and 2 produces different complexation products initially, although eventually the same TEAF complexes are produced as via sequential TEAHCO3 and TBAF addition. These findings are rationalized in terms of the formation of different ion pair complexes involving interactions both inside and outside of the core receptor framework.

References

Apr 1, 1981·Physiological Reviews·A Roos, W F Boron
Jul 21, 1998·Endocrinology and Metabolism Clinics of North America·M Kleerekoper
Oct 6, 2000·BMJ : British Medical Journal·M S McDonaghJ Kleijnen
Nov 1, 2000·Nature·D M Sigman, E A Boyle
Sep 12, 2001·Trends in Endocrinology and Metabolism : TEM·J H ZippinJ Buck
Nov 21, 2002·Biochemistry and Cell Biology = Biochimie Et Biologie Cellulaire·Richard D Vaughan-Jones, Kenneth W Spitzer
Nov 13, 2003·Chemical Reviews·Ramón Martínez-Máñez, Félix Sancenón
Apr 6, 2006·Journal of the American Chemical Society·Iwao SuzukiAkiyo Yamauchi
Sep 14, 2006·Journal of the American Chemical Society·Jonathan L SesslerPhilip A Gale
Oct 31, 2006·Angewandte Chemie·Sung Ok KangKristin Bowman-James
Dec 19, 2006·Lancet·P Grandjean, P J Landrigan
Jan 12, 2007·Biochemistry and Cell Biology = Biochimie Et Biologie Cellulaire·Joseph R Casey
Apr 11, 2008·Chemical Communications : Chem Comm·Chang-Hee LeeJonathan L Sessler
Jan 27, 2009·Chemical Society Reviews·Claudia Caltagirone, Philip A Gale
Apr 25, 2009·Biological Trace Element Research·R SandhuS Kharb
May 25, 2010·Current Medicinal Chemistry·E GazzanoD Ghigo
Jul 24, 2010·Chemico-biological Interactions·Olivier BarbierLuz María Del Razo
Sep 8, 2010·Chemical Society Reviews·Philip A Gale
Sep 8, 2010·Chemical Society Reviews·Sung Ok KangKristin Bowman-James
Dec 15, 2010·The Journal of Organic Chemistry·Sung Kuk KimJonathan L Sessler
Nov 15, 2011·Chemical Society Reviews·Marco WenzelPhilip A Gale
Oct 11, 2013·Chemical Society Reviews·Philip A GaleIsabelle L Kirby
Jul 1, 2014·Chemical Society Reviews·Philip A Gale, Claudia Caltagirone
Jul 1, 2014·Accounts of Chemical Research·Sung Kuk Kim, Jonathan L Sessler
Sep 13, 2014·Journal of Pharmaceutical Sciences·Brian J KriegGregory E Amidon
Jan 21, 2020·Chemical Society Reviews·Sangshan PengJonathan L Sessler

❮ Previous
Next ❯

Citations

Mar 4, 2021·Journal of the American Chemical Society·Han XieJovica D Badjić

❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography
X-ray
NMR

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.