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Trehalosamine
Trehalosamines are amino sugars in which a hydroxyl group of trehalose is replaced with an amino group. While 2-, 3-, and 4-trehalosamine derived from actinomycetes have been reported as natural compounds, 6-trehalosamine has been reported as a synthetic compound. They have weak antimicrobial activity and could be considered as a class of aminoglycoside antibiotics. The properties and functions of 4-trehalosamine have been well investigated as follows. Protective activity As "a trehalose possessing an amino group", trehalosamine shares many properties and characteristics in common with trehalose; in addition, unique functions due to the presence of an amino group are also suggested. Trehalose is used as a protective agent for starch, protein, cells, or tissues due to its non-reducing sugar moiety having lower non-specific reactivity than reducing sugars and high moisturizing and protective activities. In many cases, 4-trehalosamine exhibits these protective activities either com ...
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Amino Sugar
In organic chemistry, an amino sugar is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being N-Acetylglucosamine, ''N''-acetyl--glucosamine (a 2-amino-2-deoxysugar), which is the main component of chitin. Derivatives of amine containing sugars, such as N-acetylglucosamine, ''N''-acetylglucosamine and sialic acid, whose Nitrogen, nitrogens are part of more complex functional groups rather than formally being amines, are also considered amino sugars. Aminoglycosides are a class of antimicrobial compounds that inhibit bacterial protein synthesis. These compounds are conjugates of amino sugars and aminocyclitols. Synthesis From glycals Glycals are cyclic enol ether derivatives of monosaccharides, having a double bond between carbon atoms 1 and 2 of the ring. ''N''-functionalized of glycals at the C2 position, combined with glycosidic bond formation at C1 is a common strategy for the ...
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Trehalose
Trehalose (from Turkish '' tıgala'' – a sugar derived from insect cocoons + -ose) is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water. Trehalose has high water retention capabilities, and is used in food, cosmetics and as a drug. Structure Trehalose is a disaccharide formed by a bond between two α-glucose units. It is found in nature as a disaccharide and also as a monomer in some polymers. Two other stereoisomers exist: α,β-trehalose, also called ''neotrehalose'', and β,β-trehalose, also called ''isotrehalose''. Neither of these alternate isomers has been isolated from living organisms, but isotrehalose has been was found in starch hydroisolates. Synthesis At least three biological pathways support trehalose biosynthesis. An industrial process can derive trehalose from corn starch. Properties ...
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Trehalase
The enzyme Trehalase is a glycoside hydrolase, produced by cells in the brush border of the small intestine, which catalyzes the conversion of trehalose to glucose. It is found in most animals. The non-reducing disaccharide trehalose (α-D-glucopyranosyl-1,1-α-D-glucopyranoside) is one of the most important storage carbohydrates, and is produced by almost all forms of life except mammals. The disaccharide is hydrolyzed into two molecules of glucose by the enzyme trehalase. There are two types of trehalases found in ''Saccharomyces cerevisiae'', viz. neutral trehalase (NT) and acid trehalase (AT) classified according to their pH optima NT has an optimum pH of 7.0, while that of AT is 4.5. Recently it has been reported that more than 90% of total AT activity in S. cerevisiae is extracellular and cleaves extracellular trehalose into glucose in the periplasmic space. Trehalose hydrolysis One molecule of trehalose is hydrolyzed to two molecules of glucose by the enzyme trehalase. ...
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IMCTA-C14
IMCTA-C14 is an ''N''- tetradecyl (C14) derivative of trehalosamine, a bacterial metabolite. It was synthesized as a sugar-based surfactant containing a trehalose substructure from the condensation of 4-trehalosamine and tetradecanal. Its surfactant properties are not very different from those of other sugar-based surfactant with aliphatic chains of similar length. However, IMCTA-C14 shows similar biological activity to trehalose at low concentrations. For the induction of autophagy in cultured cells, trehalose is required at a high concentration of about 10-100 mM. In contrast, IMCTA-C14 shows similar activity at about 1/3000 of that concentration. To illustrate this, expression of the metabolic clock gene, ''Period'' 1, was induced more strongly in cultured hepatocytes at a concentration 1/1000 that of trehalose. The reason for its strong biological activity is thought to be that it has a fatty chain length similar to that of the phospholipids that make up the cell membrane, an ...
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Amino Sugars
In organic chemistry, an amino sugar is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being ''N''-acetyl--glucosamine (a 2-amino-2-deoxysugar), which is the main component of chitin Chitin (carbon, C8hydrogen, H13oxygen, O5nitrogen, N)n ( ) is a long-chain polymer of N-Acetylglucosamine, ''N''-acetylglucosamine, an amide derivative of glucose. Chitin is the second most abundant polysaccharide in nature (behind only cell .... Derivatives of amine containing sugars, such as N-acetylglucosamine, ''N''-acetylglucosamine and sialic acid, whose Nitrogen, nitrogens are part of more complex functional groups rather than formally being amines, are also considered amino sugars. Aminoglycosides are a class of antimicrobial compounds that inhibit bacterial protein synthesis. These compounds are conjugates of amino sugars and aminocyclitols. Synthesis From glycals Glycals are cycli ...
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Hydroxyl Group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this ...
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Amino Group
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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Actinomycete
The Actinomycetales is an order of Actinomycetota. A member of the order is often called an actinomycete. Actinomycetales are generally gram-positive and anaerobic and have mycelia in a filamentous and branching growth pattern. Some actinomycetes can form rod- or coccoid-shaped forms, while others can form spores on aerial hyphae. Actinomycetales bacteria can be infected by bacteriophages, which are called actinophages. Actinomycetales can range from harmless bacteria to pathogens with resistance to antibiotics. Reproduction Actinomycetales have 2 main forms of reproduction: spore formation and hyphae fragmentation. During reproduction, Actinomycetales can form conidiophores, sporangiospores, and oidiospores. In reproducing through hyphae fragmentation, the hyphae formed by Actinomycetales can be a fifth to half the size of fungal hyphae, and bear long spore chains. Presence and associations Actinomycetales can be found mostly in soil and decaying organic matter, as well as in l ...
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Aminoglycoside
Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar). The term can also refer more generally to any organic molecule that contains amino sugar substructures. Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic bacilli where resistance has not yet arisen but generally not against Gram-positive and anaerobic Gram-negative bacteria.ME Levison, MD, 2012, Aminoglycosides, The Merck Manua accessed 22 February 2014. Streptomycin is the first-in-class aminoglycoside antibiotic. It is derived from ''Streptomyces griseus'' and is the earliest modern agent used against tuberculosis. Streptomycin lacks the common 2-deoxystreptamine moiety (image right, below) present in most other members of this class. Other examples of aminoglycosides include the deoxystreptamine-containin ...
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