Names | |
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Preferred IUPAC name 1-Methylpyridin-1-ium-2-carboxylate | |
Other names N-methyl picolinic acid betaine, Betaine homarine | |
Identifiers | |
3D model (JSmol) | |
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PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C7H7NO2 | |
Molar mass | 137.138 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Homarine (N-methyl picolinic acid betaine) is an organic compound with the chemical formula C7H7NO2. [2] It is commonly found in aquatic organisms from phytoplankton to crustaceans, although it is not found in vertebrates. [3] [4]
Homarine functions as an osmolyte by affecting the ionic strength of the cytosol and thereby maintaining osmotic pressure within the cell. [5]
Homarine may also act as a methyl group donor in the biosynthesis of various other N-methylated chemicals, such as glycine betaine and choline. The process of methyl donation converts homarine into picolinic acid and is reversible. [6]
The name of this chemical comes from the initial discovery of the molecule in 1933 in lobster tissue: [4] the word homarine as an adjective means "of, or relating to, lobsters" (i.e. genus Homarus ).
Methionine is an essential amino acid in humans.
Choline ( KOH-leen) is an essential nutrient for humans and many other animals, which was formerly classified as a B vitamin (vitamin B4). It is a structural part of phospholipids and a methyl donor in metabolic one-carbon chemistry. The compound is related to trimethylglycine in the latter respect. It is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.
Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer (in which it is used as a flavoring), but often associatively called "minty", as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. It is also produced synthetically, used as a fragrance and as a flavoring agent.
Trimethylglycine is an amino acid derivative that occurs in plants. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because, in the 19th century, it was discovered in sugar beets.
A betaine in chemistry is any neutral chemical compound with a positively charged cationic functional group that bears no hydrogen atom, such as a quaternary ammonium or phosphonium cation, and with a negatively charged functional group, such as a carboxylate group that may not be adjacent to the cationic site. Historically, the term was reserved for trimethylglycine (TMG), which is involved in methylation reactions and detoxification of homocysteine. This is a modified amino acid consisting of glycine with three methyl groups serving as methyl donor for various metabolic pathways.
Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants. It functions as an osmolyte as well as several other physiological and environmental roles have also been identified. DMSP was first identified in the marine red alga Polysiphonia fastigiata.
Dactinomycin, also known as actinomycin D, is a chemotherapy medication used to treat a number of types of cancer. This includes Wilms tumor, rhabdomyosarcoma, Ewing's sarcoma, trophoblastic neoplasm, testicular cancer, and certain types of ovarian cancer. It is given by injection into a vein.
Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. It was first isolated in 1957 as the methyl ester of jasmonic acid by the Swiss chemist Édouard Demole and his colleagues.
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known.
In enzymology, a N-acetylneuraminate 4-O-acetyltransferase is an enzyme that catalyzes the chemical reaction
In enzymology, a galactinol-sucrose galactosyltransferase is an enzyme that catalyzes the chemical reaction
Protein AMBP is a protein that in humans is encoded by the AMBP gene.
Eukaryotic elongation factor 2 is a protein that in humans is encoded by the EEF2 gene. It is the archaeal and eukaryotic counterpart of bacterial EF-G.
Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish. It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to those of choline and betaine.
Desmosterol (Cholesta-5,24-dien-3β-ol) is a lipid present in the membrane of phytoplankton and an intermediate product in cholesterol synthesis in mammal cells. Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.
Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi. Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.
Mycosporine-like amino acids (MAAs) are small secondary metabolites produced by organisms that live in environments with high volumes of sunlight, usually marine environments. The exact number of compounds within this class of natural products is yet to be determined, since they have only relatively recently been discovered and novel molecular species are constantly being discovered; however, to date their number is around 30. They are commonly described as “microbial sunscreens” although their function is believed not to be limited to sun protection. MAAs represent high potential in cosmetics, and biotechnological applications. Indeed, their UV-absorbing properties would allow to create products derived from natural photoprotectors, potentially harmless to the environment and efficient against UV damage.
Dinosterol (4α,23,24-trimethyl-5α-cholest-22E-en-3β-ol) is a 4α-methyl sterol that is produced by several genera of dinoflagellates and is rarely found in other classes of protists. The steroidal alkane, dinosterane, is the 'molecular fossil' of dinosterol, meaning that dinosterane has the same carbon skeleton as dinosterol, but lacks dinosterol's hydroxyl group and olefin functionality. As such, dinosterane is often used as a biomarker to identify the presence of dinoflagelletes in sediments.
In biochemistry, non-coded or non-proteinogenic amino acids are distinct from the 22 proteinogenic amino acids, which are naturally encoded in the genome of organisms for the assembly of proteins. However, over 140 non-proteinogenic amino acids occur naturally in proteins and thousands more may occur in nature or be synthesized in the laboratory. Chemically synthesized amino acids can be called unnatural amino acids. Unnatural amino acids can be synthetically prepared from their native analogs via modifications such as amine alkylation, side chain substitution, structural bond extension cyclization, and isosteric replacements within the amino acid backbone. Many non-proteinogenic amino acids are important:
Chlorophyllide a and Chlorophyllide b are the biosynthetic precursors of chlorophyll a and chlorophyll b respectively. Their propionic acid groups are converted to phytyl esters by the enzyme chlorophyll synthase in the final step of the pathway. Thus the main interest in these chemical compounds has been in the study of chlorophyll biosynthesis in plants, algae and cyanobacteria. Chlorophyllide a is also an intermediate in the biosynthesis of bacteriochlorophylls.