CO2 Adducts of Certain Amino Acids, Peptides, and Sperm Whale Myoglobin Studied by Carbon 13 and Proton Nuclear Magnetic Resonance

Morrow, Jon S.; Keim, Philip; Gurd, Frank R. N.

doi:10.1016/s0021-9258(19)81264-4

Cited by 85 publications

(30 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this context, it is possible to calculate the fraction of an amino acid that would be carbamylated by CO 2 for a given set of conditions (Figure ). For the present-day value of total dissolved CO 2 in oceans (2.2 mM) and an amine p K a of 9.13 (the reported value for Ser), the fraction of carbamylated amine would be less than 5% at any pH . However, the atmospheric CO 2 concentration on the prebiotic earth has been proposed to be 100- to 1000-fold higher (∼0.35–0.07 atm) than on present-day Earth (0.0035 atm). , Using a total dissolved CO 2 concentration of 220 mM, the fraction of carbamylated amine could be as high as 75%, depending on the pH of the solution.…”

Section: Prebiotic Formation Of Peptidesmentioning

confidence: 84%

Prebiotic Peptides: Molecular Hubs in the Origin of Life

et al. 2020

View full text Add to dashboard Cite

The fundamental roles that peptides and proteins play in today’s biology makes it almost indisputable that peptides were key players in the origin of life. Insofar as it is appropriate to extrapolate back from extant biology to the prebiotic world, one must acknowledge the critical importance that interconnected molecular networks, likely with peptides as key components, would have played in life’s origin. In this review, we summarize chemical processes involving peptides that could have contributed to early chemical evolution, with an emphasis on molecular interactions between peptides and other classes of organic molecules. We first summarize mechanisms by which amino acids and similar building blocks could have been produced and elaborated into proto-peptides. Next, non-covalent interactions of peptides with other peptides as well as with nucleic acids, lipids, carbohydrates, metal ions, and aromatic molecules are discussed in relation to the possible roles of such interactions in chemical evolution of structure and function. Finally, we describe research involving structural alternatives to peptides and covalent adducts between amino acids/peptides and other classes of molecules. We propose that ample future breakthroughs in origin-of-life chemistry will stem from investigations of interconnected chemical systems in which synergistic interactions between different classes of molecules emerge.

show abstract

Section: Prebiotic Formation Of Peptidesmentioning

confidence: 84%

Prebiotic Peptides: Molecular Hubs in the Origin of Life

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Mass spectrometry-based proteomics is a powerful tool for discovering and exploring PTMs. Although carbamylation of neutral N -terminal α-amino or lysine ε-amino groups may be a “ general and functionally important phenomenon throughout biology ” ( Morrow et al, 1974 ) and “ form the basis for a widespread mechanism of biological regulation ” ( Lorimer, 1983 ), the transient and readily reversible nature of this PTM all but renders impossible the use of mass spectrometry-based proteomics workflows (even when soft ionisation techniques are utilised; Terrier and Douglas, 2010 ). This ready reversibility limits our discovery of the distribution and contribution of carbamylation to biological functions.…”

Section: Mass Spectrometry Approaches For the Identification Of Carba...mentioning

confidence: 99%

“…This carbamate post-translational modification (PTM) is critical to regulating oxygen-binding in haemoglobin and the activation of the CO 2 -fixing enzyme RuBisCO. It has been suggested that protein carbamylation could form the basis of a widespread mechanism for biological regulation ( Morrow et al, 1974 ; Lorimer, 1983 ). Computational studies predict that carbamates may be found in more than 1.3% of large proteins ( Jimenez-Morales et al, 2014 ).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Carbon Dioxide and the Carbamate Post-Translational Modification

Blake

Cann

2022

Front. Mol. Biosci.

View full text Add to dashboard Cite

Carbon dioxide is essential for life. It is at the beginning of every life process as a substrate of photosynthesis. It is at the end of every life process as the product of post-mortem decay. Therefore, it is not surprising that this gas regulates such diverse processes as cellular chemical reactions, transport, maintenance of the cellular environment, and behaviour. Carbon dioxide is a strategically important research target relevant to crop responses to environmental change, insect vector-borne disease and public health. However, we know little of carbon dioxide’s direct interactions with the cell. The carbamate post-translational modification, mediated by the nucleophilic attack by carbon dioxide on N-terminal α-amino groups or the lysine ɛ-amino groups, is one mechanism by which carbon dioxide might alter protein function to form part of a sensing and signalling mechanism. We detail known protein carbamates, including the history of their discovery. Further, we describe recent studies on new techniques to isolate this problematic post-translational modification.

show abstract

“…However, degeneration, poor regeneration capacity, and absorbent loss on repetitive use of amines during CO 2 capture have motivated the search for alternatives materials. Amino acids (AA) and ionic liquids (ILs) − have been explored as viable choices to characterize CO 2 absorption since the start of the 21st century. In one of the noteworthy works, Ohno and co-workers synthesized a series of imidazolium cation based amino acid ILs (AAILs) which incorporates the advantages of ILs (eco-friendly) and AA (CO 2 affinity).…”

Section: Introductionmentioning

confidence: 99%

Site-Specific Interactions in CO₂ Capture by Lysinate Anion and Role of Water Using Density Functional Theory

Prakash

Venkatnathan

2018

J. Phys. Chem. C

View full text Add to dashboard Cite

The understanding of mechanism of reactions between the [Lys]− anion and CO2 is important for the optimization and design of salt mixtures and ionic liquids for facile CO2 capture. In this computational investigation, we employed density functional theory calculations to examine various reaction pathways associated with site-specific interactions possible in [Lys]−–CO2 and [Lys]−–H2O–CO2 complexes. The reaction mechanisms in each complex are characterized by energy parameters such as binding energy (BE), activation energy (E a), and reaction energy (RE). The [Lys]−–CO2 interactions lead to the formation of three nonbonded (NB) complexes close to the near-carboxylate amine group (N1) and one NB complex close to the far-carboxylate amine group (N2). The N1 site reacts with CO2 with a small barrier of ∼1 kcal/mol to form a stable “carbamate–carboxylic acid” product. The formation of this product is due to an intramolecular proton transfer from the N1 amine site to the carboxylate group (COO–), in contrast to the intermolecular proton transfer for carbamic acid formation observed from the N2–CO2 reaction. The other two NB complexes show significant stability due to multiple-site-cooperative interactions of CO2 with the COO– group and N1 site. In [Lys]−–H2O–CO2 interactions, nine NB complexes are formed corresponding to different weak interactions. Among them, five NB complexes lead to reactions suggesting chemisorption, with four complexes forming a direct bicarbonate product and the remaining complex forming a carbamate–carboxylic acid product. The other four nonreactive complexes show notable stability due to the formation of multiple hydrogen bonds with the inclusion of water, which alludes to their possibility of occurrence in physisorption.

show abstract

CO2 Adducts of Certain Amino Acids, Peptides, and Sperm Whale Myoglobin Studied by Carbon 13 and Proton Nuclear Magnetic Resonance

Cited by 85 publications

References 60 publications

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Carbon Dioxide and the Carbamate Post-Translational Modification

Site-Specific Interactions in CO₂ Capture by Lysinate Anion and Role of Water Using Density Functional Theory

Contact Info

Product

Resources

About

CO2 Adducts of Certain Amino Acids, Peptides, and Sperm Whale Myoglobin Studied by Carbon 13 and Proton Nuclear Magnetic Resonance

Cited by 85 publications

References 60 publications

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Carbon Dioxide and the Carbamate Post-Translational Modification

Site-Specific Interactions in CO2 Capture by Lysinate Anion and Role of Water Using Density Functional Theory

Contact Info

Product

Resources

About

Site-Specific Interactions in CO₂ Capture by Lysinate Anion and Role of Water Using Density Functional Theory