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Topic: Glycosidic bond

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Leaving group

Acetal

Cytidine

SN2 reaction

Activated complex

Sucrose

Sugar

Disaccharide

Chemical bond

Ionic bond

Inosine

Thioesters

Carbohydrate

Transition state

Glucose

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	Glycoside - Wikipedia, the free encyclopedia
		In chemistry, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via an O-glycosidic bond or an S-glycosidic bond; the latter are also called thioglycosides.
		Glycosides play many important roles in living organisms, and numerous plant-produced glycosides are used as medications.
		Many authors require in addition that the sugar be bonded to a non-sugar for the molecule to qualify as a glycoside, thus excluding the polysaccharides.
	en.wikipedia.org /wiki/Glycoside (638 words)

	[No title] (Site not responding. Last check: 2007-11-06)
		Cellobiose is a stereoisomer of maltose with beta-stereochemistry at the glycosidic linkage.
		Lactose is formed from a molecule of galactose and a molecule of glucose that are linked by a glycosidic bond from the hydroxy group (O is blue) on carbon 4 (gold) of the glucose to carbon 1 (the acetal carbon, green) of the galactose with beta stereochemistry.
		It differs from the other disaccharides in that its glycosidic bond is formed between carbon 1 (the acetal carbon, green in the model) of glucose and carbon 2 (the acetal carbon, blue in the model) of fructose.
	www.du.edu /~jhornbac/organic/disaccharides.html (345 words)

	Glycosidic bond - Wikipedia, the free encyclopedia
		In chemistry, a glycosidic bond is a certain type of chemical bond that joins a sugar molecule to another molecule.
		Specifically, a glycosidic bond is formed between the hemiacetal group of a saccharide (or a molecule derived from a saccharide) and the hydroxyl group of an alcohol.
		A glycosidic bond can join two monosaccharide molecules to form a disaccharide, as for instance in the linkage of glucose and fructose to create sucrose.
	en.wikipedia.org /wiki/Glycosidic_bond (638 words)

	Encyclopedia: Glycosidic bond
		A chemical bond is the phenomenon of atoms being held together in molecules, crystals or in solid metal.
		A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom.
		A glucoside is a glycoside that is derived from glucose.
	www.nationmaster.com /encyclopedia/Glycosidic-bond (586 words)

	Glycosidic bond (Site not responding. Last check: 2007-11-06)
		A glycosidic bond is formed between a hemiacetal group of asugar molecule (such as glucose) and an alcohol functional group to form an acetal.
		A N-glycosidic bond is formed between the hemiacetal group of a sugarmolecule (such as ribose) and a N-H group on an aromatic ring.
		A water molecule is extracted (causing a dehydration reaction), and a bond is formed, leaving an oxygen atom between the two monosaccharides, andcreating a disaccharide.
	www.therfcc.org /glycosidic-bond-106527.html (148 words)

	[No title] (Site not responding. Last check: 2007-11-06)
		Bond angles of 90 degrees are not consistent with a tetrahedral geometry.
		The cation is bonded in an octahedral geometry.
		A 10.25: The bond length in succinate is 1.55 angstroms, and in fumarate, 1.34 angstroms.
	www.bimcore.emory.edu /home/Kins/EMS/ANSWERS.txt (13366 words)

	Extracellular polysaccharides MCQ answer
		The free energy associated with the glycosidic bond in maltose is 4 kcal/mol whereas the free energy associated with the glycosidic bond of sucrose is 7 kcal/mol.
		The free energy associated with the glycosidic bond of sucrose is, therefore, equivalent to that of phosphorylated precursors used in intracellular synthetic pathways and is sufficient to provide 3.2 kcal/mol required to sequentially add glucose or fructose units to the growing EPS chain.
		The glycosidic bond in maltose links C1 and C4 of two glucose units and the free energy associated with the hydrolysis of the bond is 4 kcal/mol.
	www.ncl.ac.uk /dental/oralbiol/oralenv/mcqs/oralmicro/eps2.htm (1680 words)

	Carbohydrates
		This bond is generally between the number 1 carbon of one monosaccharide and the number 4 carbon of the other molecule.
		There is an alternate form of a glycosidic bond (the 1-4 beta-glycosidic bond) between two glucose molecules that is structurally different from the alpha form.
		Because of the structure of glycosidic bonds, the two monosaccharides in a disaccharide do not have to be the same.
	www.austincc.edu /~emeyerth/carbohyd.htm (786 words)

	SparkNotes: Carbohydrates: Types of Carbohydrates
		The type of bond that is formed between the two sugars is called a glycosidic bond.
		The bond formed between the two monosaccharides is called a beta glycosidic bond (figure 1.3).
		The alpha glycosidic bond, found in sucrose and maltose, differs from the beta glycosidic bond only in the angle of formation between the two sugars.
	www.sparknotes.com /health/carbohydrates/section1.html (1327 words)

	Read about Glycosidic bond at WorldVillage Encyclopedia. Research Glycosidic bond and learn about Glycosidic bond here! (Site not responding. Last check: 2007-11-06)
		A glycosidic bond is formed between a hemiacetal group of a sugar molecule (such as glucose) and an alcohol functional group to form an
		An N-glycosidic bond is formed between the hemiacetal group of a sugar molecule (such as ribose) and an N-H group on an
		molecule is extracted (causing a dehydration reaction), and a bond is formed, leaving an oxygen atom between the two monosaccharides, and creating a disaccharide.
	encyclopedia.worldvillage.com /s/b/Glycosidic (196 words)

	United States Patent Application: 0040106772
		The glycopeptide antibiotics are further categorized into various subclasses depending on the identity and interconnections of the amino acids comprising the peptide backbone and the number and substitution pattern of the sugar residues in the molecule.
		[0056] A "glycosyl donor" is a sugar or glycosidic residue that bears an anomeric leaving group, preferably a sulfoxide, which may be activated to render the anomeric carbon susceptible to reaction with a nucleophile to displace the activated group, thereby forming a glycosidic bond.
		Most preferably, Y is a single bond and X is NR.sub.1 or S, i.e., a substituted amino or thio group is attached to the C-6 position of the hexose.
	appft1.uspto.gov /netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=/netahtml/PTO/srchnum.html&r=1&f=G&l=50&s1="20040106772".PGNR.&OS=DN/20040106772&RS=DN/20040106772 (14241 words)

	PSC 3110 Glycosides
		The formation of a glycosidic bond between a sugar and an alcohol is a non-reversible reaction under normal conditions.
		In other words, the glycosidic bond will not spontaneously break and re-produce the reducing sugar and alcohol unless you use an enzyme or chemical method to cleave the glycosidic bond.
		The dietary carbohydrates are converted to monosaccharides by enzymes "glycosidases" that hydrolyze the glycosidic bonds between the sugars.
	wiz2.pharm.wayne.edu /biochem/311glycosidestrfxn.html (1258 words)

	Carbohydrates and Proteins
		Glucose and Fructose are joined by a glycosidic bond between their carbonyl carbons.
		The peptide bond is an amide bond; this is formed by condensation of an amine with a carboxyl group by the elimination of a molecule of water.
		Disulfide Bonds: Many protein structures are stabilized by intrachain disulfide bonds formed between 2 molecules of Cysteine to form 1 Cystine; this crosslinks different parts of the polypeptide.
	www.sci.sdsu.edu /class/bio202/TFrey/CH2O_Proteins.html (2048 words)

	Phosphorylase recognition and phosphorolysis of its oligosaccharide substrate: answers to a long outstanding question
		(1−4) glycosidic bond in glycogen or oligosaccharide substrates.
		Protonation of the glycosidic oxygen, between subsites -1 and +1, results in cleavage of the glycosidic bond and formation of a carbonium−oxonium ion transition state that is favoured and stabilized by the now negatively charged phosphate.
		The constellation of the cofactor 5'-phosphate, the inorganic phosphate and the glycosidic linkage of the thio-oligosaccharide are fully consistent with the mechanism shown in Figure 8, in which general acid attack on the glycosidic linkage is promoted by the cofactor phosphate via exchange of a proton between the two phosphate groups.
	www.nature.com /emboj/journal/v18/n17/full/7591874a.html (9154 words)

	We are what we eat learning resource
		They are used in conjunction with terms such as glycosidic bond, anomer (alpha and beta anomers) and to described certain bonds (e.g.
		In the case of sucrose this is an a1:2 glycosidic bond.
		This bond is broken during digestion by the enzyme b-galactosidase to release the free sugars glucose and galactose.
	florey.biosci.uq.edu.au /GMC/macromol.html (2284 words)

	Chemistry : Chapter 12 : Overview (Site not responding. Last check: 2007-11-06)
		Functional groups involving oxygen include alcohols, where an OH group (hydroxyl group) is bonded to a carbon, and ethers, where there is a carbon–oxygen–carbon bond.
		A molecule that has a carbon bonded to both a hydroxyl group and the oxygen of an ether is called a hemiacetal.
		If the carbonyl carbon is also bonded to a hydroxyl group, it is a carboxylic acid, and if the carbon is bonded to two other carbons, it is a ketone.
	www.wwnorton.com /chemistry/overview/ch12.htm (1894 words)

	The carbon has three sigma bonds in a plane, and a p-bond formed from overlap of the filled p-orbital on the carbon and ... (Site not responding. Last check: 2007-11-06)
		Cellulose is a polymer of b-(D)-glucose with b(1→4) glycosidic bonds.
		The b(1→4) glycosidic bonds in cellulose result in straight linear polymer suitable for the structural parallel plant fibres.
		Whilst in starch and glycogen the glucose monomers are linked by a(1→4) glycosidic bonds that result in a spiral or helical structure that is appropriate as a food source/store by plants and mammals.
	www.le.ac.uk /chemistry/teach/year1/LECT9.html (495 words)

	Toner and developer for electrophotography - US Patent 6455217 (Site not responding. Last check: 2007-11-06)
		This is because hydrogen bonding properties resulting from the presence of hydroxyl groups in a molecule of the polysaccharides are remarkably strong, and crystallizability is extremely high.
		As a matter of course, a cyclodextrin, that is, a precursor of the ethyl cyclic oligosaccharide for use in the present invention, is not soluble in a wax.
		Therefore, the intermolecular bond strength is remarkably high and the crystallizability is high, with the result that the molecular chain is rigid.
	www.patentstorm.us /patents/6455217.html (6637 words)

	Polysaccharide Conformations
		Since its position is of importance in specifying the unit, the torsion angle at the glycosidic bond is included in the characteristics of the sugar residue (section 2.2).
		The glycosidic linkage is most easily described using the symbols for the monomeric units and the locants together with the anomeric descriptor, e.g.
		Fig.4 Notation for the torsion angles specifying the orientation of glycosidic bonds for a pyranose unit (A) varrying a ring hydroxyl that is glycosylated and (B) in which the glycosylated hydroxyl group is on an exocyclic carbon.
	www.chem.qmul.ac.uk /iupac/misc/psac.html (1735 words)

	Glycosidic bond cleavage of 5-fluoro-2'-deoxyuridine and 5-fluorouridine by amino acyl-tRNA synthetases. (Site not responding. Last check: 2007-11-06)
		Glycosidic bond cleavage of 5-fluoro-2'-deoxyuridine and 5-fluorouridine by amino acyl-tRNA synthetases.
		Glycosidic bond cleavage of 5-fluoro-2'-deoxyuridine and 5-fluorouridine by amino acyl-tRNA synthetases.The generation of 5-Fluorouracil was monitored by cellulose thin layer chromatography and by spectrophotometry.
		Lysyl-tRNA synthetase isolated from rat liver cleaves glycosidic bond of 5-Fluorouridine and 5-Fluoro-2'-deoxyuridine to generate 5-Fluorouracil.
	www.pdg.cnb.uam.es /UniPub/iHOP/gp/6803477.html (70 words)

	CHE 415 - General Biochemistry I - Mechanisms of Substrate Recognition by Enzymes
		The cleavage of the NAM-NAG bond by lysozyme occurs through hydrolysis, the addition of a water molecule across the ether linkage, such that two hydroxyl groups result.
		O label was consistently incorporated into the 1-hydroxyl group of the NAM residue, indicating that the bond broken was that connecting the 1-carbon of NAM to the oxygen atom in the glycosidic linkage.
		Based on the crystallographic data and later experiments designed to check hypotheses concerning the roles of specific amino acid residues, it was determined that the key histidine residues, His12 and His119, assist in the hydrolysis of the phosphodiester linkage by trading protons through the substrate.
	people.uis.edu /efish1/Che415/Lectur14/lectur14.htm (2543 words)

	dec2.html
		The new bond between the two sugars is known as the glycosidic bond.
		This is because all the chains and braches finish in a sugar whose anomeric carbon is involved in the glycosidic bond.
		The preffered conformation of the glycosidic bonds is
	tonga.usip.edu /gmoyna/biochem341/lecture34.html (2729 words)

	Botany online: Macromolecules - Glucanes containing beta - glycosidic Linkage (Site not responding. Last check: 2007-11-06)
		Neighbouring cellulose chains may form hydrogen bonds leading to the formation of microfibrils with partially crystalline parts (micelles).
		This type of bond causes the polymer to arrange in a helix.
		It is only exceptionally found in plants, like in some algae (see theme 44) but it is the main structural component of the cell walls of most fungi.
	www.biologie.uni-hamburg.de /b-online/e17/17c.htm (141 words)

	Polynucleotide Conformations 2
		The backbone of a polynucleotide chain consists of a repeating unit of six single bonds as shown in Fig.
		the O4'-C1' bond is eclipsed with the N9-C4 bond for purine and the N1-C2 bond for pyrimidine derivatives.
		Y. The polarity of a hydrogen bond is from the hydrogen-atom donor to the acceptor.
	www.chem.qmw.ac.uk /iupac/misc/noGreek/pnuc2.html (2291 words)

	Enzymatic Synthesis of Carbon-Fluorine Bonds (Site not responding. Last check: 2007-11-06)
		It is probable that this difference arises from a hydrogen bond to the serine hydroxyl group.
		Likewise, a hydrogen bond formed with the departing fluoride ion in the glycosynthase transition state (Scheme 1, second step) may also explain the ~25-fold greater glycosynthase activity of Man2A and Abg serine mutants relative to the alanine mutants.
		The catalysis of carbon-fluorine bond formation by mutants of two unrelated glycosidases, each using a nucleophilic fluorination mechanism, demonstrates the feasibility of such a mechanism occurring in Nature.
	pubs.acs.org /cgi-bin/jcen?jacsat/123/i18/html/ja005855q.html (1670 words)

	Carbohydrates
		The glucose residues are linked by a glycosidic bond between their #1 and #4 carbon atoms.
		At approximately every thirtieth residue along the chain, a short side chain is attached by a glycosidic bond to the #6 carbon atom (the carbon above the ring).
		Because of the orientation of the glycosidic bonds linking the glucose residues, the rings of glucose are arranged in a flip-flop manner.
	users.rcn.com /jkimball.ma.ultranet/BiologyPages/C/Carbohydrates.html (828 words)

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