Ion pair formation of phosphorylated amino acids and lysine and arginine side chains: a theoretical study

Proteins
J Mavri, H J Vogel

Abstract

Protein phosphorylation is one of the major signal transduction mechanisms for controlling and regulating intracellular processes. Phosphorylation of specific hydroxylated amino acid side chains (Ser, Thr, Tyr) by protein kinases can activate numerous enzymes; this effect can be reversed by the action of protein phosphatases. Here we report ab initio (HF/6-31G and Becke3LYP/6-31G) and semiempirical (PM3) molecular orbital calculations pertinent to the ion pair formation of the phosphorylated amino acids with the basic side chains of Lys and Arg. Methyl-, ethyl-, and phenylphosphate, as well as methylamine and methylguanidinium were used as model compounds for the phosphorylated and basic amino acids, respectively. Phosphorylated amino acids were calculated as mono- and divalent anions. Our results indicate that the PSer/PThr ion pair interaction energies are stronger than those with PTyr. Moreover, the interaction energies with the amino group of Lys are generally more favorable than with the guanidinium group of Arg. The Lys amino groups form stable bifurcated hydrogen bonded structures; while the Arg guanidinium group can form a bidentate hydrogen bonded structure. Reasonable values for the interaction free energies in aqueou...Continue Reading

References

Dec 1, 1992·Journal of Computer-aided Molecular Design·C J Cramer, D G Truhlar
Oct 30, 1992·Cell·T Pawson, G D Gish
Jan 1, 1992·Annual Review of Biochemistry·C Norbury, P Nurse
Nov 15, 1991·Biochimica Et Biophysica Acta·H Saint-MartinL Adamowicz
Mar 1, 1990·Journal of Computer-aided Molecular Design·J J Stewart
Sep 1, 1990·Trends in Biochemical Sciences·B E Kemp, R B Pearson
Jan 1, 1989·Methods in Enzymology·H J Vogel
Oct 1, 1981·International Journal of Peptide and Protein Research·D M Salunke, M Vijayan
Apr 1, 1994·Current Opinion in Cell Biology·D O Morgan, H L De Bondt
May 15, 1994·Structure·S S Taylor, E Radzio-Andzelm
Mar 11, 1994·Science·D BarfordN K Tonks
Jan 1, 1993·Annual Review of Biophysics and Biomolecular Structure·L N Johnson, D Barford
Jan 1, 1993·Annual Review of Biophysics and Biomolecular Structure·G D Rose, R Wolfenden

❮ Previous
Next ❯

Citations

Dec 6, 2006·Antimicrobial Agents and Chemotherapy·Zhigang LiuNeville R Kallenbach
Jun 1, 2014·Biochimica Et Biophysica Acta·Konstantin AndreevDavid Gidalevitz
Mar 5, 2003·Pharmacological Reviews·Michael R Yeaman, Nannette Y Yount
Mar 23, 2002·Biochemistry and Cell Biology = Biochimie Et Biologie Cellulaire·Hans J VogelRichard M Epand
Sep 26, 2019·Annals of the New York Academy of Sciences·Anandhi Anandan, Alice Vrielink
Nov 15, 2020·The Journal of Chemical Physics·Ilya G Shenderovich
Feb 19, 2002·Chemical Reviews·Christopher J. Cramer, Donald G. Truhlar
Dec 11, 1999·Biochimica Et Biophysica Acta·R M Epand, H J Vogel
Jun 24, 2015·The Journal of Physical Chemistry. B·Marta WiśniewskaMariusz Makowski
Jan 25, 2007·Journal of the American Chemical Society·Daniel J MandellMatthew P Jacobson
Jan 28, 2003·Biophysical Journal·M WojciechowskiB Lesyng

❮ 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.