Biochemical processes which introduce C=O groups into proteins
See also: Carbonylation
In biochemistry, protein carbonylation refers to oxidation of the side chains of proteins to introduce ketone (>C=O) and aldehyde (−CH=O) groups in a protein. The following amino acid residues are affected:
prolyl to pyrrolidone
glutamyl to glutamic semialdehyde
lysyl to aminoadipic acid semialdehyde
threonyl to amino ketobutyric acid
Carbonylation is typically assumed to be the result of reactive oxygen species (ROS) attacking the protein side chain. ROS species include hydroperoxide or lipic hydroperoxides. Protein carbonylation is of interest because of its association with various diseases.[1] Oxidative stress, often metal catalyzed, leads to protein carbonylation.
^Dalle-Donne, Isabella; Aldini, Giancarlo; Carini, Marina; Colombo, Roberto; Rossi, Ranieri; Milzani, Aldo (2006). "Protein carbonylation, cellular dysfunction, and disease progression". Journal of Cellular and Molecular Medicine. 10 (2): 389–406. doi:10.1111/j.1582-4934.2006.tb00407.x. PMC 3933129. PMID 16796807. Grimsrud, P. A.; Xie, H.; Griffin, T. J.; Bernlohr, D. A. (2008). "Oxidative Stress and Covalent Modification of Protein with Bioactive Aldehydes". Journal of Biological Chemistry. 283 (32): 21837–41. doi:10.1074/jbc.R700019200. PMC 2494933. PMID 18445586.
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biochemistry, proteincarbonylation refers to oxidation of the side chains of proteins to introduce ketone (>C=O) and aldehyde (−CH=O) groups in a protein. The...
term carbonylation also refers to oxidation of protein side chains. Several industrially useful organic chemicals are prepared by carbonylations, which...
derivative that can be used as a probe for the determination of proteincarbonylation. It readily forms Schiff bases with carbonyl groups. Madian, Ashraf...
Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, Milzani A (2006). "Proteincarbonylation, cellular dysfunction, and disease progression". Journal of Cellular...
biochemical alterations, like increased proteincarbonylation and high levels of Glial fibrillary acidic protein (GFAP), which in NAGM areas comes together...
to proteins in the PDB Swedish Chemicals Agency. Information sheet – Acetic Acid Process Flow sheet of Acetic acid Production by the Carbonylation of...
the Mitsunobu reaction, using thioacetic acid. They also arise via carbonylation of alkynes and alkenes in the presence of thiols. Thioesters hydrolyze...
used on a smaller scale because they require specialized equipment. Carbonylation of alcohols as illustrated by the Cativa process for the production...
Because of the low-cost and large-scale availability of formic acid by carbonylation of methanol and hydrolysis of the resulting methyl formate, sodium formate...
industry by diverse means. Acetic anhydride is mainly produced by the carbonylation of methyl acetate. Maleic anhydride is produced by the oxidation of...
Raney nickel or palladium on carbon to lead into the key-step, the carbonylation of 1-(4-isobutylphenyl)ethanol. This is achieved by a PdCl2(PPh3)2 catalyst...
approaches use a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde), for its low cost. It is also prepared by the reaction...
include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Succinate is also produced from butane via maleic...
metabolized in the liver primarily by oxidation via hydroxylation and carbonylation. It is also secondarily metabolized to produce glucuronide conjugates...
similar β subunits. These three types show very similar oxygenation and carbonylation properties, which are unaffected by urea, an important compound in marine...
polyamides, and isocyanates are derived via acid-base catalysis. Most carbonylation processes require metal catalysts, examples include the Monsanto acetic...
process. Hydroformylation and the acetic acid syntheses are two of myriad carbonylation processes. Breath carbon monoxide – Level of carbon monoxide in exhaled...
AlIII with simultaneous ring opening by the [Co(CO)4]− counterion. Carbonylation of the resultant alkylcobalt followed by lactonization releases the...
trimerisation to benzene, tetramerization to cyclooctatetraene, and carbonylation to hydroquinone: Fe(CO)5 + 4 C2H2 + 2 H2O → 2 C6H4(OH)2 + FeCO3 at basic...
or triple bonds. OsO4 + 4 H2 → Os + 4 H2O OsO4 undergoes "reductive carbonylation" with carbon monoxide in methanol at 400 K and 200 sbar to produce the...
converts the methanol feedstock into methyl iodide, which undergoes carbonylation. Hydrolysis of the resulting acetyl iodide regenerates hydroiodic acid...
from acetaldehyde, is made predominantly by the lower-cost methanol carbonylation process. The impact on demand has led to increase in prices and thus...
oxidation than ferrocene. Cobalt carbonyl (Co2(CO)8) is a catalyst in carbonylation and hydrosilylation reactions. Vitamin B12 (see below) is an organometallic...
radioactive isotope to the molecule. For instance a palladium catalysed carbonylation reaction in a microfluidic device has been used to rapidly form amides...
polymerization, cyclohexane oxidation to adipic acid, and butadiene carbonylation to nylon intermediates. Approaches to catalyst systems have included...
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