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Anomer
In carbohydrate chemistry, a pair of anomers () is a pair of near-identical stereoisomers that differ at only the anomeric carbon, the carbon 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 is planar and thus achiral. More formally stated, then, an anomer is an epimer at the hemiacetal/hemiketal carbon 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 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 hemiacetals is the anomeric carbon C-1; in he ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Anomeric Effect
In organic chemistry, the anomeric effect or Edward-Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring 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 an OH group pointing up equatorially, and the ''alpha'' anomer having that OH group pointing down axially. The anomeric effect can also be generalized to any cyclohexyl or linear syst ... [...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 optical is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbohydrate Chemistry
Carbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the detection, synthesis, structure, and function of carbohydrates. Due to the general structure of carbohydrates, their synthesis is often preoccupied with the selective formation of glycosidic linkages and the selective reaction of hydroxyl groups; as a result, it relies heavily on the use of protecting groups. Monosaccharides Individual saccharide residues are termed monosaccharides. Carbohydrate synthesis Carbohydrate synthesis is a sub-field of organic chemistry concerned specifically with the generation of natural and unnatural carbohydrate structures. This can include the synthesis of monosaccharide residues or structures containing more than one monosaccharide, known as oligosaccharides. Glycosidic bond formation * Chemical glycosylation * Fischer glycosidation * Glycosyl halide * Koenigs-Knorr reaction Protecting groups * Carbohydrate acetalisation * Trimethylsilyl * Benzyl Eth ... [...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. Simi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mutarotation
Mutarotation is the change in the '' optical rotation'' because of the change in the equilibrium between two anomers, when the corresponding stereocenters interconvert. 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 and their ratio in the solution. For example, if a solution of β-D-glucopyranose ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mannose
Mannose is a sugar monomer of the aldohexose series of carbohydrates. It is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation are associated with mutations in enzymes involved in mannose metabolism. Mannose is not an essential nutrient; it can be produced in the human body from glucose, or converted into glucose. Mannose provides 2–5 kcal/g. It is partially excreted in the urine. Etymology The root of both "mannose" and "mannitol" is manna, which the Bible describes as the food supplied to the Israelites during their journey in the region of Sinai. Several trees and shrubs can produce a substance called manna, such as the "manna tree" ('' Fraxinus ornus'') from whose secretions mannitol was originally isolated. Structure Mannose commonly exists as two different-sized rings, the pyranose (six-membered) form and the furanose (five-membered) form. E ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dipole
In physics, a dipole () is an electromagnetic phenomenon which occurs in two ways: *An electric dipole deals with the separation of the positive and negative electric charges found in any electromagnetic system. A simple example of this system is a pair of charges of equal magnitude but opposite sign separated by some typically small distance. (A permanent electric dipole is called an electret.) *A magnetic dipole is the closed circulation of an electric current system. A simple example is a single loop of wire with constant current through it. A bar magnet is an example of a magnet with a permanent magnetic dipole moment. Dipoles, whether electric or magnetic, can be characterized by their dipole moment, a vector quantity. For the simple electric dipole, the electric dipole moment points from the negative charge towards the positive charge, and has a magnitude equal to the strength of each charge times the separation between the charges. (To be precise: for the definition of t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrogen Bonds
In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a lone pair of electrons—the hydrogen bond acceptor (Ac). Such an interacting system is generally denoted , where the solid line denotes a polar covalent bond, and the dotted or dashed line indicates the hydrogen bond. The most frequent donor and acceptor atoms are the second-row elements nitrogen (N), oxygen (O), and fluorine (F). Hydrogen bonds can be intermolecular (occurring between separate molecules) or intramolecular (occurring among parts of the same molecule). The energy of a hydrogen bond depends on the geometry, the environment, and the nature of the specific donor and acceptor atoms and can vary between 1 and 40 kcal/mol. This makes them somewhat stronger than a van der Waals interaction, and weaker than fully covalent o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pyranose
Pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom. There may be other carbons external to the ring. The name derives from its similarity to the oxygen heterocycle pyran, but the pyranose ring does not have double bonds. A pyranose in which the anomeric OH at C(l) has been converted into an OR group is called a pyranoside. Formation The pyranose ring is formed by the reaction of the hydroxyl group on carbon 5 (C-5) of a sugar with the aldehyde at carbon 1. This forms an intramolecular hemiacetal. If reaction is between the C-4 hydroxyl and the aldehyde, a furanose is formed instead. The pyranose form is thermodynamically more stable than the furanose form, which can be seen by the distribution of these two cyclic forms in solution. History Hermann Emil Fischer won the Nobel Prize in Chemistry (1902) for his work in determining the structure of the D- aldohexoses ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclohexane Conformation
In organic chemistry, cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide range of compounds. The internal angles of a regular, flat hexagon are 120°, while the preferred angle between successive bonds in a carbon chain is about 109.5°, the tetrahedral angle (the arc cosine of −). Therefore, the cyclohexane ring tends to assume non-planar (warped) conformations, which have all angles closer to 109.5° and therefore a lower strain energy than the flat hexagonal shape. Consider the carbon atoms numbered from 1 to 6 around the ring. If we hold carbon atoms 1, 2, and 3 stationary, with the correct bond lengths and the tetrahedral angle between the two bonds, and then continue by adding carbon atoms 4, 5, and 6 with the correct bond length and the tetrahedral angle, we can ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Axis Of Rotation
Rotation around a fixed axis is a special case of rotational motion. The fixed- axis hypothesis excludes the possibility of an axis changing its orientation and cannot describe such phenomena as wobbling or precession. According to Euler's rotation theorem, simultaneous rotation along a number of stationary axes at the same time is impossible; if two rotations are forced at the same time, a new axis of rotation will appear. This article assumes that the rotation is also stable, such that no torque is required to keep it going. The kinematics and dynamics of rotation around a fixed axis of a rigid body are mathematically much simpler than those for free rotation of a rigid body; they are entirely analogous to those of linear motion along a single fixed direction, which is not true for ''free rotation of a rigid body''. The expressions for the kinetic energy of the object, and for the forces on the parts of the object, are also simpler for rotation around a fixed axis, than ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
