S-Methylcysteine Sulfoxide
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S-Methylcysteine Sulfoxide
''S''-Methylcysteine sulfoxide is an organosulfur compound with the formula . It is the sulfoxide of ''S''-methylcysteine. It contributes to the flavor of onions (''Allium'' sp.). The compound is usually encountered as one diastereoisomer, the (''R'')- and (''S'')-configurations at the carbon and sulfur stereocenters, respectively. The ''S''-methyl part of the name refers to the location of the methyl group on sulfur. Although odorless, S-methylcysteine sulfoxide is acted upon by alliinase and lachrymatory-factor synthase. ''S''-Methylcysteine sulfoxide is produced from glutathione. Related compounds are the unsaturated sulfoxides ''S''-''trans''-prop-1-enyl cysteine sulfoxide and ''S''-propyl cysteine sulfoxide, both found also in onions, and ''S''-allyl cysteine sulfoxide, typically found in garlic Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh on ...
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Organosulfur Compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two ( cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and car ...
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Sulfoxide
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent. Structure and bonding Sulfoxides feature relatively short S–O distances. In DMSO, the S–O distance is 1.531 Å. The sulfur center is pyramidal; the sum of the angles at sulfur is about 306°.. Sulfoxides are generally represented with the structural formula R−S(=O)−R', where R and R' are organic groups. The bond between the sulfur and oxygen atoms is intermediate of a dative bond and a polarized double bond. The double-bond resonance form implies 10 electrons around sulfur (10-S-3 in N-X-L notation). The double-bond character of the S−O bond may be accou ...
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S-Methylcysteine
''S''-Methylcysteine is the amino acid with the nominal formula CH3SCH2CH(NH2)CO2H. It is the S-methylated derivative of cysteine. This amino acid occurs widely in plants, including many edible vegetables. Natural occurrence S-Methylcysteine is not genetically coded, but it arises by post-translational methylation of cysteine. One pathway involves methyl transfer from alkylated DNA by zinc-cysteinate-containing repair enzymes such as methylated-DNA-protein-cysteine methyltransferase. S-Methylcysteine sulfoxide is an oxidized derivative of S-methylcysteine that is found in onions. MetaCyc contains a list of biochemical reactions producing and consuming this substance. Other chemical properties Beyond its biological context, S-methylcysteine has been examined as a chelating agent Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bon ...
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Onion
An onion (''Allium cepa'' , from Latin ), also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus '' Allium''. The shallot is a botanical variety of the onion which was classified as a separate species until 2011. The onion's close relatives include garlic, scallion, leek, and chives. The genus contains several other species variously called onions and cultivated for food, such as the Japanese bunching onion '' Allium fistulosum'', the tree onion ''Allium'' × ''proliferum'', and the Canada onion '' Allium canadense''. The name '' wild onion'' is applied to a number of ''Allium'' species, but ''A. cepa'' is exclusively known from cultivation. Its ancestral wild original form is not known, although escapes from cultivation have become established in some regions. The onion is most frequently a biennial or a perennial plant, but is usually treated as an annual and harvested in its first growing season. ...
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Allium
''Allium'' is a large genus of monocotyledonous flowering plants with around 1000 accepted species, making ''Allium'' the largest genus in the family Amaryllidaceae and among the largest plant genera in the world. Many of the species are edible, and some have a long history of cultivation and human consumption as a vegetable including the onion, garlic, scallion, scallions, shallot, shallots, leek, leeks, and chives, with onions being the second most grown vegetable globally after tomatoes as of 2023. ''Allium'' species occur in temperate climates of the Northern Hemisphere, except for a few species occurring in Chile (such as ''A. juncifolium''), Brazil (''A. sellovianum''), and tropical Africa (Allium spathaceum, ''A. spathaceum''). They vary in height between . The flowers form an umbel at the top of a leafless stalk. The bulbs vary in size between species, from small (around 2–3 mm in diameter) to rather large (8–10 cm). Some species (such as Wels ...
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Diastereoisomer
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus typically increases the number of stereoisomers by a factor of two. Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers that differ in all stereocenters and are therefore mirror images of one another. Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding the opposing enantiomer). Diastereomers h ...
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Alliinase
In enzymology, an alliin lyase () is an enzyme that catalyzes the chemical reaction :an ''S''-alkyl-L-cysteine ''S''-oxide \rightleftharpoons an alkyl sulfenate + 2-aminoacrylate Hence, this enzyme has one substrate, ''S''-alkyl-L-cysteine ''S''-oxide, and two products, alkyl sulfenate and 2-aminoacrylate. This enzyme belongs to the family of lyases, specifically the class of carbon-sulfur lyases. The systematic name of this enzyme class is ''S''-alkyl-L-cysteine ''S''-oxide alkyl-sulfenate-lyase (2-aminoacrylate-forming). Other names in common use include alliinase, cysteine sulfoxide lyase, alkylcysteine sulfoxide lyase, ''S''-alkylcysteine sulfoxide lyase, L-cysteine sulfoxide lyase, ''S''-alkyl-L-cysteine sulfoxide lyase, and alliin alkyl-sulfenate-lyase. It employs one cofactor, pyridoxal phosphate. Many alliinases contain a novel ''N''-terminal epidermal growth factor-like domain ( EGF-like domain). Occurrence These enzymes are found in plants of the genus ' ...
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Glutathione
Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and cysteine. The carboxyl group of the cysteine residue is attached by normal peptide linkage to glycine. Biosynthesis and occurrence Glutathione biosynthesis involves two adenosine triphosphate-dependent steps: *First, γ-glutamylcysteine is synthesized from L-glutamate and L-cysteine. This conversion requires the enzyme glutamate–cysteine ligase (GCL, glutamate cysteine synthase). This reaction is the rate-limiting step in glutathione synthesis. *Second, glycine is added to the C-terminal of γ-glutamylcysteine. This condensation is ca ...
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Garlic
Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh onion, and Chinese onion. Garlic is native to central and south Asia, stretching from the Black Sea through the southern Caucasus, northeastern Iran, and the Hindu Kush; it also grows wild in parts of Mediterranean Europe. There are two subspecies and hundreds of varieties of garlic. Garlic has been used for thousands of years as a seasoning, culinary ingredient, traditional medical remedy; it was known in many ancient civilizations, including the Babylonians, Egyptians, Romans, and Chinese, and remains significant in many cuisines and folk treatments, especially across the Mediterranean and Asia. Garlic propagates in a variety of climates and conditions and is produced globally; China is by far the largest producer, accounting for over two thirds (73%) of the world's supply in 2021. Description Garli ...
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Sulfur Amino Acids
Sulfur (American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with the chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature. Sulfur is the tenth most abundant element by mass in the universe and the fifth most common on Earth. Though sometimes found in pure, native form, sulfur on Earth usually occurs as sulfide and sulfate minerals. Being abundant in native form, sulfur was known in ancient times, being mentioned for its uses in ancient India, ancient Greece, China, and ancient Egypt. Historically and in literature sulfur is also called brimstone, which means "burning stone". Almost all elemental sulfur is produced as a byproduct of removing sulfur-containing contaminants from natural gas and petroleum.. Downloahere The greates ...
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Sulfoxides
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a Chemical polarity, polar functional group. Sulfoxides are oxidized Derivative (chemistry), derivatives of thioether, sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent. Structure and bonding Sulfoxides feature relatively short S–O distances. In DMSO, the S–O distance is 1.531 Å. The sulfur center is pyramidal; the sum of the angles at sulfur is about 306°.. Sulfoxides are generally represented with the structural formula R−S(=O)−R', where R and R' are organic groups. The bond between the sulfur and oxygen atoms is intermediate of a dative bond and a polarized double bond. The double-bond resonance form implies 10 electrons around sulfur (10-S-3 in N-X-L notation). The dou ...
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Alpha-Amino Acids
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 appear in the genetic code of life. Amino acids can be classified according to the locations of the core structural functional groups ( alpha- , beta- , gamma- amino acids, etc.); other categories relate to polarity, ionization, and side-chain group type ( aliphatic, acyclic, aromatic, polar, etc.). In the form of proteins, amino-acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life on Earth and its emergence. Amino acids are formally named by the IUPAC- IUBMB Joint Commiss ...
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