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Anomer
In carbohydrate chemistry, a pair of anomers () is a pair of near-identical stereoisomers or diastereomers that differ at only the anomeric carbon, the carbon atom that bears the aldehyde or ketone functional group in the sugar's open-chain form. However, in order for anomers to exist, the sugar must be in its cyclic form, since in open-chain form, the anomeric carbon atom is planar and thus achiral. More formally stated, then, an anomer is an epimer at the hemiacetal/hemiketal carbon atom in a cyclic saccharide. Anomerization is the process of conversion of one anomer to the other. As is typical for stereoisomeric compounds, different anomers have different physical properties, melting points and specific rotations. Nomenclature Every two anomers are designated alpha (α) or beta (β), according to the configurational relationship between the ''anomeric centre'' and the ''anomeric reference atom'', hence they are relative stereodescriptors. The anomeric centre in hemiac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Anomeric Effect
In organic chemistry, the anomeric effect or Edward-Lemieux effect (after J. T. Edward and Raymond Lemieux) is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to the heteroatom in the ring in, e.g., tetrahydropyran to prefer the ''axial'' orientation instead of the less-hindered ''equatorial'' orientation that would be expected from steric considerations. This effect was originally observed in pyranose rings by J. T. Edward in 1955 when studying carbohydrate chemistry. The term ''anomeric effect'' was introduced in 1958. The name comes from the term used to designate the lowest-numbered ring carbon of a pyranose, the ''anomeric'' carbon. Isomers that differ only in the configuration at the anomeric carbon are called ''anomers''. The anomers of D-glucopyranose are diastereomers, with the ''beta'' anomer having a hydroxyl () group pointing up equatorially, and the ''alpha'' anomer having that () group pointing down axially. The anomer ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereoisomers
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer. Enantiomers Enantiomers, also known as optical isomers, are two stereoisomers that are related to each other by a reflection: they are mirror images of each other that are non-superposable. Human hands are a macroscopic analog of this. Every stereogenic center in one has the opposite configuration in the other. Two compounds that are enantiomers of each other have the same physical properties, except for the direction in which they rotate polarized light and how they interact with different enantiomers ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Epimer
In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is the interconversion of one epimer to the other epimer. Doxorubicin and epirubicin are two epimers that are used as drugs. Examples The stereoisomers β-D- glucopyranose and β-D- mannopyranose are epimers because they differ only in the stereochemistry at the C-2 position. The hydroxy group in β-D-glucopyranose is equatorial (in the "plane" of the ring), while in β-D-mannopyranose the C-2 hydroxy group is axial (up from the "plane" of the ring). These two molecules are epimers but, because they are not mirror images of each other, are not enantiomers. (Enantiomers have the same name, but differ in D and L classification.) They are also not sugar anomers, since it is not the anomeric carbon involved in the stereochemistry. Simila ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mutarotation
In stereochemistry, mutarotation is the change in optical rotation of a chiral material in a solution due to a change in proportion of the two constituent anomers (i.e. the interconversion of their respective stereocenters) until equilibrium is reached. Cyclic sugars show mutarotation as α and β anomeric forms interconvert. The optical rotation of the solution depends on the optical rotation of each anomer and their ratio in the solution. Mutarotation was discovered by French chemist Augustin-Pierre Dubrunfaut in 1844, when he noticed that the specific rotation of aqueous sugar solution changes with time. Measurement The α and β anomers are diastereomers of each other and usually have different specific rotations. A solution or liquid sample of a pure α anomer will rotate plane polarised light by a different amount and/or in the opposite direction than the pure β anomer of that compound. The optical rotation of the solution depends on the optical rotation of each anomer ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbohydrate Chemistry
A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' may differ). This formula does not imply direct covalent bonding between hydrogen and oxygen atoms; for example, in , hydrogen is covalently bonded to carbon, not oxygen. While the 2:1 hydrogen-to-oxygen ratio is characteristic of many carbohydrates, exceptions exist. For instance, uronic acids and deoxy-sugars like fucose deviate from this precise stoichiometric definition. Conversely, some compounds conforming to this definition, such as formaldehyde and acetic acid, are not classified as carbohydrates. The term is predominantly used in biochemistry, functioning as a synonym for saccharide (), a group that includes sugars, starch, and cellulose. The saccharides are divided into four chemical groups: monosaccharides, disaccharides, oligosa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oxocarbenium
In organic chemistry, an oxocarbenium ion (alternatively spelled oxacarbenium) is a chemical species characterized by a central sp2-hybridized atom of carbon, a substituent atom of oxygen, and an overall positive charge that is delocalized between the central carbon and oxygen atoms (). An oxocarbenium ion is represented by two limiting resonance structures, one in the form of a carbenium ion with the positive charge on carbon () and the other in the form of an oxonium species with the formal charge on oxygen (). As a resonance hybrid, the true structure falls between the two. Compared to neutral carbonyl () compounds like ketones () or esters, the carbenium ion form is a larger contributor to the structure. They are common reactive intermediates in the hydrolysis of glycosidic bonds, and are a commonly used strategy for chemical glycosylation. These ions have since been proposed as reactive intermediates in a wide range of chemical transformations, and have been utilized in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
D-galactose
Galactose (, '' galacto-'' + ''-ose'', ), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecule linked with a glucose molecule forms a lactose molecule. Galactan is a polymeric form of galactose found in hemicellulose, and forming the core of the galactans, a class of natural polymeric carbohydrates. D-Galactose is also known as brain sugar since it is a component of glycoproteins (oligosaccharide-protein compounds) found in nerve tissue. Etymology The word ''galactose'' was coined by Charles Weissman in the mid-19th century and is derived from Greek , , and the generic chemical suffix for sugars ''-ose''. The etymology is comparable to that of the word ''lactose'' in that both contain roots meaning "milk sugar". Lactose is a disaccharide of galactose plus glucose. Structure and isomerism Galactose exists in both open-chain and cyclic form ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Specific Rotation
In chemistry, specific rotation ( �'') is a property of a chiral chemical compound. It is defined as the change in orientation of monochromatic plane-polarized light, per unit distance–concentration product, as the light passes through a sample of a compound in solution. Compounds which rotate the plane of polarization of a beam of plane polarized light clockwise are said to be dextrorotary, and correspond with positive specific rotation values, while compounds which rotate the plane of polarization of plane polarized light counterclockwise are said to be levorotary, and correspond with negative values. If a compound is able to rotate the plane of polarization of plane-polarized light, it is said to be “ optically active”. Specific rotation is an intensive property, distinguishing it from the more general phenomenon of optical rotation. As such, the ''observed'' rotation (α) of a sample of a compound can be used to quantify the enantiomeric excess of that compound, prov ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Equilibrium
In a chemical reaction, chemical equilibrium is the state in which both the Reagent, reactants and Product (chemistry), products are present in concentrations which have no further tendency to change with time, so that there is no observable change in the properties of the Thermodynamic system, system. This state results when the forward reaction proceeds at the same rate as the Reversible reaction, reverse reaction. The reaction rates of the forward and backward reactions are generally not zero, but they are equal. Thus, there are no net changes in the concentrations of the reactants and products. Such a state is known as dynamic equilibrium. It is the subject of study of ''equilibrium chemistry''. Historical introduction The Concept learning, concept of chemical equilibrium was developed in 1803, after Claude Louis Berthollet, Berthollet found that some chemical reactions are Reversible reaction, reversible. For any reaction mixture to exist at equilibrium, the reaction rate, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Degree (angle)
A degree (in full, a degree of arc, arc degree, or arcdegree), usually denoted by ° (the degree symbol), is a measurement of a plane (mathematics), plane angle in which one Turn (geometry), full rotation is 360 degrees. It is not an SI unit—the SI unit of angular measure is the radian—but it is mentioned in the SI Brochure, SI brochure as an Non-SI units mentioned in the SI, accepted unit. Because a full rotation equals 2 radians, one degree is equivalent to radians. History The original motivation for choosing the degree as a unit of rotations and angles is unknown. One theory states that it is related to the fact that 360 is approximately the number of days in a year. Ancient astronomers noticed that the sun, which follows through the ecliptic path over the course of the year, seems to advance in its path by approximately one degree each day. Some ancient calendars, such as the Iranian calendar, Persian calendar and the Babylonian calendar, used 360 days for a year. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diastereomer
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
