α-Cyclodextrin
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α-Cyclodextrin
α-Cyclodextrin (''alpha''-cyclodextrin), sometimes abbreviated as α-CD, is a hexasaccharide derived from glucose. It is related to the β- (beta) and γ- (gamma) cyclodextrins, which contain seven and eight glucose units, respectively. All cyclodextrins are white, water-soluble solids with minimal toxicity. Cyclodextrins tend to bind other molecules in their quasi-cylindrical interiors. This inclusion (and release) behavior leads to applications in medicine. The compound is of wide interest because it exhibits host–guest properties, forming inclusion compounds. Structure In α-cyclodextrin, the six glucose subunits are linked end to end via α-1, 4 linkages. The result has the shape of a tapered cylinder, with six primary alcohols on one face and twelve secondary alcohol groups on the other. The exterior surface of cyclodextrins is somewhat hydrophilic whereas the interior core is hydrophobic. Applications α-Cyclodextrin is marketed for a range of medical, healthcare, ...
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Cyclodextrin
Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds. Cyclodextrins are produced from starch by enzymatic conversion. They are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering. Cyclodextrins are composed of 5 or more α-D-glucopyranoside units linked 1->4, as in amylose (a fragment of starch). Typical cyclodextrins contain a number of glucose monomers ranging from six to eight units in a ring, creating a cone shape: * α (alpha)-cyclodextrin: 6 glucose subunits * β (beta)-cyclodextrin: 7 glucose subunits * γ (gamma)-cyclodextrin: 8 glucose subunits The largest well-characterized cyclodextrin contains 32 1,4-anhydroglucopyranoside units. Poorly-characterized mixtures, containing at least 150-membered cyclic oligosaccharides are also known. Applications Drug delivery Cyclodextrins are ingredients in more than 30 d ...
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Saccharide
In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or may not be different from ''n''), which does not mean the H has covalent bonds with O (for example with , H has a covalent bond with C but not with O). However, not all carbohydrates conform to this precise stoichiometric definition (e.g., uronic acids, deoxy-sugars such as fucose), nor are all chemicals that do conform to this definition automatically classified as carbohydrates (e.g. formaldehyde and acetic acid). The term is most common in biochemistry, where it is a synonym of saccharide (), a group that includes sugars, starch, and cellulose. The saccharides are divided into four chemical groups: monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides and disaccharides, the smallest (lower molecular weight) ...
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Glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Gluco ...
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Inclusion Compound
In host–guest chemistry, an inclusion compound (also known as an inclusion complex) is a chemical complex in which one chemical compound (the "host") has a cavity into which a "guest" compound can be accommodated. The interaction between the host and guest involves purely van der Waals bonding. The definition of inclusion compounds is very broad, extending to channels formed between molecules in a crystal lattice in which guest molecules can fit. Examples and case studies Calixarenes Calixarenes and related formaldehyde-arene condensates are one class of hosts that form inclusion compounds. One famous illustration is the adduct with cyclobutadiene, which otherwise is unstable. Cyclodextrins Cyclodextrins are well established hosts for the formation of inclusion compounds. Illustrative is the case of ferrocene which is inserted into the cyclodextrin at 100 °C under hydrothermal conditions. Cyclodextrin also forms inclusion compounds with fragrances. As a result, the f ...
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Rotaxane Crystal Structure ChemComm Page493 2001 Commons
In chemistry, a rotaxane () is a mechanically interlocked molecular architecture consisting of a dumbbell-shaped molecule which is threaded through a macrocycle (see graphical representation). The two components of a rotaxane are kinetically trapped since the ends of the dumbbell (often called ''stoppers'') are larger than the internal diameter of the ring and prevent dissociation (unthreading) of the components since this would require significant distortion of the covalent bonds. Much of the research concerning rotaxanes and other mechanically interlocked molecular architectures, such as catenanes, has been focused on their efficient synthesis or their utilization as artificial molecular machines. However, examples of rotaxane substructure have been found in naturally occurring peptides, including: cystine knot peptides, cyclotides or lasso-peptides such as microcin J25. Synthesis The earliest reported synthesis of a rotaxane in 1967 relied on the statistical probability t ...
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Cyclodextrin Glycosyltransferase
In enzymology, a cyclomaltodextrin glucanotransferase (also cyclodextrin glycosyl transferase or CGTase for short) () is an enzyme that catalyzes the chemical reaction of cyclizing part of a 1,4-alpha-D-glucan molecule through the formation of a 1,4-alpha-D-glucosidic bond. They are bacterial enzymes belonging to the same family of the α-amylase specifically known as glycosyl-hydrolase family 13. This peculiar enzyme is capable of catalyzing more than one reaction with the most important being the synthesis of non-reducing cyclic dextrins known as cyclodextrins starting from starch, amylose, and other polysaccharides. CGTase is an enzyme common to many bacterial species, in particular of the ''Bacillus'' genus (e.g. ''B. circulans'', ''B. macerans'' and ''B. stearothermophilus'') and ''Brevibacillus brevis.'' This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is 1,4-alpha-D-glucan 4-alpha-D- ...
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β-Cyclodextrin
β-Cyclodextrin sometimes abbreviated as β-CD, is a heptasaccharide derived from glucose. The α- (alpha), β- (beta), and γ- (gamma) cyclodextrins correspond to six, seven, and eight glucose units, respectively. β-Cyclodextrin is the most used natural cyclodextrin in marketed medicines. The reason for this lies in the ease of its production and subsequent low price (more than 10,000 tons produced annually with an average bulk price of approximately 5 USD per kg). Structure In β-cyclodextrin, the seven glucose subunits are linked end to end via α-1,4 linkages. The result has the shape of a tapered cylinder, with seven primary alcohols on one face and fourteen secondary alcohol groups on the other. The exterior surface of cyclodextrins is somewhat hydrophilic whereas the interior core is hydrophobic. Physical properties β-Cyclodextrin exists as a white (colorless) powder or crystals. The density of its saturated hydrate crystal (βCD·12H2O) is 1.46 g/cm3. β-Cyclodextri ...
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Oligosaccharides
An oligosaccharide (/ˌɑlɪgoʊˈsækəˌɹaɪd/; from the Greek ὀλίγος ''olígos'', "a few", and σάκχαρ ''sácchar'', "sugar") is a saccharide polymer containing a small number (typically two to ten) of monosaccharides (simple sugars). Oligosaccharides can have many functions including cell recognition and cell adhesion. They are normally present as glycans: oligosaccharide chains are linked to lipids or to compatible amino acid side chains in proteins, by ''N''- or ''O''-glycosidic bonds. ''N''-Linked oligosaccharides are always pentasaccharides attached to asparagine via a beta linkage to the amine nitrogen of the side chain.. Alternately, ''O''-linked oligosaccharides are generally attached to threonine or serine on the alcohol group of the side chain. Not all natural oligosaccharides occur as components of glycoproteins or glycolipids. Some, such as the raffinose series, occur as storage or transport carbohydrates in plants. Others, such as maltodextrins or c ...
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