Alkali metal ion binding to amino acids versus their methyl esters: affinity trends and structural changes in the gas phase

Chemistry : a European Journal
Jody M TalleyC Wesdemiotis

Abstract

The relative alkali metal ion (M(+)) affinities (binding energies) between seventeen different amino acids (AA) and the corresponding methyl esters (AAOMe) were determined in the gas phase by the kinetic method based on the dissociation of AA-M(+)-AAOMe heterodimers (M=Li, Na, K, Cs). With the exception of proline, the Li(+), Na(+), and K(+) affinities of the other aliphatic amino acids increase in the order AA<AAOMe, while their Cs(+) affinities generally decrease in this direction. For aliphatic beta-amino acids, which are particularly basic molecules, the order AA>AAOMe is already observed for K(+). Proline binds more strongly than its methyl ester to all M(+) except Li(+). Ab initio calculations on the M(+) complexes of alanine, beta-aminoisobutyric acid, proline, glycine methyl ester, alanine methyl ester, and proline methyl ester show that their energetically most favorable complexes result from charge solvation, except for proline which forms salt bridges. The most stable mode of charge solvation depends on the ligand (AA or AAOMe) and, for AA, it gradually changes with metal ion size. Esters chelate all M(+) ions through the amine and carbonyl groups. Amino acids coordinate Li(+) and Na(+) ions through the amine and car...Continue Reading

References

Feb 1, 1988·Molecular and Cellular Biochemistry·H Z ChenG Zubay
Sep 19, 2000·Chemistry : a European Journal·T B McMahon, G Ohanessian
Dec 16, 2000·Journal of the American Society for Mass Spectrometry·V RyzhovC Wesdemiotis
Dec 1, 1994·Journal of the American Society for Mass Spectrometry·S Beranová, C Wesdemiotis

❮ Previous
Next ❯

Citations

Jul 6, 2004·Journal of the American Society for Mass Spectrometry·Andrew S Lemoff, Evan R Williams
Feb 8, 2005·Journal of the American Society for Mass Spectrometry·Seonghee AhnScott Gronert
Dec 13, 2006·Journal of the American Society for Mass Spectrometry·Ping WangGilles Ohanessian
Oct 12, 2007·Journal of the American Society for Mass Spectrometry·Henryk Wincel
Mar 10, 2016·Chemical Reviews·M T Rodgers, P B Armentrout
Apr 9, 2009·Mass Spectrometry Reviews·Ronghu Wu, Terry B McMahon
Nov 13, 2007·Journal of Mass Spectrometry : JMS·Ping WangChrys Wesdemiotis
Nov 3, 2015·Physical Chemistry Chemical Physics : PCCP·S HeilesEvan R Williams
Oct 7, 2003·Mass Spectrometry Reviews·Lorenza Operti, Roberto Rabezzana
Jun 11, 2005·European Journal of Mass Spectrometry·Emily E Jellen, Victor Ryzhov
May 31, 2018·Physical Chemistry Chemical Physics : PCCP·Sven HeilesEvan R Williams
Feb 23, 2008·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Nick C PolferRobert C Dunbar
Nov 13, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Jesús JoverJoaquim Sales
Jul 5, 2005·Chemistry : a European Journal·Seduraman AbiramiNgai Ling Ma
Sep 8, 2010·Physical Chemistry Chemical Physics : PCCP·Robert C DunbarJos Oomens
Aug 5, 2016·The Journal of Biological Chemistry·Yongqiang ZhangKe Dong
Feb 3, 2005·Journal of Mass Spectrometry : JMS·M BelcastroM Toscano
Mar 28, 2008·The Journal of Physical Chemistry. a·S J Ye, P B Armentrout
May 1, 2008·Journal of the American Chemical Society·Matthew F BushEvan R Williams
Jul 13, 2006·The Journal of Physical Chemistry. a·S AbiramiN L Ma
Jul 13, 2006·The Journal of Physical Chemistry. a·Andrew S LemoffEvan R Williams
Nov 6, 2008·The Journal of Physical Chemistry. a·Miriam K DrayssMathias Schäfer
Jan 7, 2009·The Journal of Physical Chemistry. a·Robert C DunbarJos Oomens
Jul 30, 2009·The Journal of Physical Chemistry. a·Miriam K DrayssMathias Schäfer
Feb 21, 2007·Journal of the American Chemical Society·Aude SimonTerrance B McMahon
Jul 25, 2009·Journal of the American Chemical Society·James S PrellEvan R Williams
Aug 29, 2009·The Journal of Organic Chemistry·Adrian L SchwanAmir Nasser Ahmadi
Mar 29, 2012·The Journal of Physical Chemistry. a·P B ArmentroutM T Rodgers
Jun 8, 2012·The Journal of Physical Chemistry. a·Lingbiao MengZijing Lin
Aug 31, 2011·The Journal of Physical Chemistry. B·Michael B BurtTravis D Fridgen
Oct 13, 2007·Journal of the American Chemical Society·Matthew F BushEvan R Williams

❮ 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.