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Topic: Anomeric carbon

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	The Anomeric Effect
		The anomeric effect was initially defined as the preference for an electronegative substituent, at the anomeric carbon in a carbohydrate, to be in an axial rather than equatorial orientation.
		It is noteworthy to mention that the conformation of the substituent at the anomeric carbon must be such that a lone pair orbital is anti-periplanar to the antibonding orbital of the bond between the anomeric carbon and the ring oxygen.
		The bond between the electronegative atom X and the anomeric carbon A can be either synclinal (axial in a ring system) to the bond between the atom which possesses lone pairs (the heteroatom in a ring system) and the R group (a bridge atom in the ring system) or anti-periplanar (equatorial in a ring system).
	euch6f.chem.emory.edu /anomericeffect.html (2865 words)

	Anomeric carbon Definition / Anomeric carbon Research (Site not responding. Last check: 2007-10-06)
		An anomeric carbon is the new stereocenterA stereocenter is a carbon atom in a chemical compound that has four different types of atoms or groups of atoms attached to each side of it.
		anomeric carbon is the carbon that is bound to the alcohol.
		anomeric carbon is the same side as the oxygen on the highest.
	www.elresearch.com /Anomeric_carbon (141 words)

	Carbon Atom (Site not responding. Last check: 2007-10-06)
		trigonaal koolstofatoom (trigonal carbon atom), tetragonaal koolstofatoom (tetragonal carbon atom), onverzadigd koolstofatoom (unsaturated C atom, unsaturated carbon atom), anomere koolstofatoom van de suiker (anomeric carbon atom of the sugar).
		atome de carbone trigonal (trigonal carbon atom), atome de carbone tétragonal (tetragonal carbon atom), atome de carbone insaturé (unsaturated carbon atom), atome de carbone anomérique du sucre (anomeric carbon atom of the sugar).
		atomo di carbonio trigonale (trigonal carbon atom), atomo di carbonio tetragonale (tetragonal carbon atom), atomo di carbonio insaturo (unsaturated C atom, unsaturated carbon atom), atomo di carbonio anomerico dello zucchero (anomeric carbon atom of the sugar).
	www.websters-online-dictionary.org /ca/carbon+atom.html (421 words)

	Glycosidic bond - Wikipedia, the free encyclopedia
		The anomeric carbon of saccharides is very reactive, and glycosidic bonds form readily in the presence of acid.
		In analogy, one also considers S-glycosidic bonds, where the anomeric carbon of a sugar is bound to some other group via a sulfur (rather than an oxygen) atom, and N-glycosidic bonds, where the anomeric carbon is bond to some other group via a nitrogen atom.
		In general, one distinguishes between α- and β-glycosidic bonds, depending on whether the original hydroxyl group of the participating anomeric carbon is in the α or β configuration.
	en.wikipedia.org /wiki/Glycosidic_bond (617 words)

	Anomeric carbon - Encyclopedia, History and Biography
		An anomeric carbon is the new stereocenter created in forming the cyclic structure of a monosaccharide.
		It is the carbon that is connected to two oxygen molecules.
		Stereoisomers that differ in configuration only at the anomeric carbon are called anomers.
	www.arikah.net /encyclopedia/Anomeric_carbon (87 words)

	The anomeric effect
		The answer is the anomeric effect, which states that electronegative substituents at the anomeric center of pyranoses prefer to adopt an axial configuration.
		The stronger the electron-withdrawing property is of the substituent on the anomeric carbon, the larger is the anomeric effect.
		For glycosyl halides the anomeric effect is round 2,5 - 3,0 kcal mol -1; while less electronegative substitutents on the anomeric carbon, give a value from 0,5 - 1,5 kcal/mol [Kirby, 1983].
	folk.uio.no /toreben/a-monohalo-ethers/Introduction/Anomeric/Anomeric.html (481 words)

	Carbon linked glycosyl compounds - US Patent 5597906 (Site not responding. Last check: 2007-10-06)
		Accordingly, the "carbonyl" carbon of an aldose or a ketose is termed the "anomeric" carbon.
		In an acetal, the anomeric carbon is located at a terminal position on the carbon backbone of the aldose.
		In a ketal, the anomeric carbon is centered at a non-terminal carbon within the backbone of the ketose.
	www.patentstorm.us /patents/5597906.html (1425 words)

	BCH 4053 Biochemistry I (Site not responding. Last check: 2007-10-06)
		The carbon thus identified as the "first" carbon in the chain is carbon #1.
		Carbon #2 is not chiral, neither is carbon 1, or carbon 5.
		This carbon is termed the anomeric carbon, and the a- and b- forms are anomers.
	wine1.sb.fsu.edu /BCH4053/Lecture12/Lecture12.htm (1951 words)

	General Biochemistry BB450/550 Oregon State University (Site not responding. Last check: 2007-10-06)
		We use the convention today that the 'D' isomer corresponds to the stereoisomer in which the lowest asymmetric carbon from the top (closest to the bottom) is written on the right side of the molecule.
		This carbon is called the anomeric carbon and it can exist in the alpha (down position) or beta (up position) configurations.
		If the hydroxyl of the anomeric carbon is altered (by methylation, for example), the linear structure cannot form and 'flipping' cannot occur.
	oregonstate.edu /instruction/bb450/lecturenoteskevin/highlightscarbohydratesI.html (510 words)

	[No title] (Site not responding. Last check: 2007-10-06)
		Do anomeric C have to be carbonyl, because you defined in your lecture that an anomeric C is a cabonyl C. The anomeric C of sugars starts out as a carbonyl in the straight chain form.
		Note that the carbon involved in anomer formation is asymmetric (has 4 different groups attached) after cyclization but was not asymmetric before cyclization, when it was a carbonyl carbon.
		One anomeric carbon mustbe involved in the formation of a glycosidic bond; the partner can be any of the non-anomeric (or anomeric) carbons.
	www.columbia.edu /cu/biology/courses/c2005/q99-01/q0201.html (269 words)

	Monosaccharides (Site not responding. Last check: 2007-10-06)
		The hemicacetal is formed when the aldehyde carbon (carbon #1) reacts with the oxygen of carbon #5 to form the ring structure.
		This reaction converts carbon #1 (anomeric carbon) into a stereocarbon, and therefore there are two different configurations for the hydroxyl group on the anomeric carbon.
		To see these differences in the structures below, position the anomeric carbons (yellow) so that they are on the extreme right hand side and the carbon which is not part of the ring (carbon #6) is above the ring.
	www.messiah.edu /departments/chemistry/molscilab/organic/monosaccarides.htm (273 words)

	Media Portfolio
		The number of carbon atoms in the sugar generally ranges from three to seven, designated by the term triose (three carbons), tetrose (four carbons), pentose (five carbons), hexose (six carbons), and heptose (seven carbons).
		The hemiacetal carbon is called the anomeric carbon, easily identified as the only carbon atom bonded to two oxygens.
		In cellobiose, the anomeric carbon of one glucose unit is linked through an equatorial (b) carbon-oxygen bond to C4 of another glucose unit.
	wps.prenhall.com /wps/media/objects/340/348272/wade_ch23.html (1687 words)

	Extracellular polysaccharides MCQ answer
		In all aldose sugars, C1 is the carbon with the aldehyde group attached and is known as the anomeric carbon atom because this structure allows for two different configurations known as anomers.
		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 reason for this is that the glycosidic bond of sucrose links both anomeric carbon atoms whereas the bond in maltose links the anomeric carbon of one glucose with C4 of another.
	www.ncl.ac.uk /dental/oralbiol/oralenv/mcqs/oralmicro/eps2.htm (1680 words)

	Chapter 25 : Carbohydrates
		The -H group (not shown) at the anomeric carbon implies the structure is based on an aldehyde, so we have an acetal.
		The anomeric carbon is attached to 2 other C atoms so the structure is based on a ketone so we have an ketal.
		The anomeric carbon is only attached to one other C atom, so it corresponds to an aldehyde.
	www.chem.ucalgary.ca /courses/351/Carey5th/Ch25/ch25-ans.html (481 words)

	Di- and Polysaccharides
		The outcome is that in a reducing sugar the anomeric carbon is in an aldehyde or hemiacetal.
		In a non-reducing sugar, the anomeric carbon is in an acetal.
		For this purpose, the hemiacetal includes the anomeric carbon of a monosaccharide and the alcohol role is played by a specific OH group of a second monosaccharide.
	chemistry2.csudh.edu /rpendarvis/dipolysacch.html (1325 words)

	Carbohydrates
		From this it was concluded that the six carbons are in an unbranched chain.
		The hemiacetal carbon atom (C-1) becomes a new stereogenic center, commonly referred to as the anomeric carbon, and the α and β-isomers are called anomers.
		The anomeric methyl glucosides are formed in an equilibrium ratio of 66% alpha to 34% beta.
	www.cem.msu.edu /~reusch/VirtualText/carbhyd.htm (4742 words)

	Lecture #1 (Site not responding. Last check: 2007-10-06)
		=4 stereoisomers of aldotetroses and 4-3=1 asymmetric carbon and 2
		The new asymmetric (chiral) carbon is known as the anomeric carbon.
		For example: maltose: glucose- (a 1-4)-glucose is formed by a glycosidic linkage of a-D-Glucose carbon #1 (the anomeric carbon) to the -OH on carbon #4 of another molecule of a-D-glucose.
	qcom.etsu.edu /GRAD/MedBiochem/01W_carbohydratres.htm (1801 words)

	Molecular Dynamics of a Flexible Polysaccharide
		C relaxation rates for the seven distinct anomeric carbon atoms in the repeating subunit of this polymer along with several different schemes for interpreting the data in terms of polymer dynamics on the picosecond to nanosecond time scale.
		The carbon frequency was set in the middle of anomeric carbon chemical shift region (125.770591 MHz) with a spectral width of 4000.0 Hz.
		Therefore the dipolar contributions of H1 and of C2 to the relaxation of the anomeric carbon atom are formally identical.
	www.research.umbc.edu /~qxu/Rch/Qjdyn/qjdyn.html (4994 words)

	Carbohydrates - Ribose
		The -OH on carbon #4 is converted into the ether linkage to close the ring with carbon #1.
		Carbon # 1 is now called the anomeric carbon and is the center of a hemiacetal functional group.
		The presence or absence of the -OH group on carbon (#2) is an important distinction between ribose and deoxyribose.
	www.elmhurst.edu /%7Echm/vchembook/543ribose.html (448 words)

	Biochem 153A: Week 4 Discussion Handout Answers
		1) A glycosidic bond originates from an anomeric carbon and is bonded to the oxygen of the hydroxyl group on something else, which can be another monosaccharide (ie glucose, fructose, etc), or a serine in a polypeptide (resulting in a glycoprotein), or an alcohol (like methanol), or glycerol (resulting in a glycolipid).
		So, if the anomeric carbon is free, that is called the reducing end (RE) of the sugar.
		Both anomeric carbons are occupied in the glycosidic bond, so this disaccharide is neither mutarotatory or capable of being a reducing agent.
	www.chem.ucla.edu /~wong/153/week4answers.html (876 words)

	[No title]
		The "C=O" carbon becomes chiral in the ring: -OH group is either down (the anomer) or up (anomer)
		Condensation reaction (with elimination of water) involving the anomeric carbon
		Anomeric carbon becomes fixed (alpha or beta) and is no longer subject to oxidation
	starklab.slu.edu /Coulter/Biochem/Carbos.htm (375 words)

	A (Site not responding. Last check: 2007-10-06)
		Stereodescriptors used in carbohydrate nomenclature to describe the configuration at the anomeric carbon by relating it to the anomeric reference atom.
		For simple cases the anomeric reference atom is the same as the configurational reference atom.
		Anomeric Effect - Originally the thermodynaniic preference for polar groups bonded to C- I (the anomeric carbon) to take up an axial position of a glycopyranosyl derivative.
	www.sdsc.edu /Education/Elemnet/misc/newerglossary/a.html (1095 words)

	Anomeric deacetylation - Patent 4855417
		Sugars substituted at the anomeric position by a hydroxyl group (1--OH) are important intermediates in the synthesis of active pharmaceuticals.
		The anomeric deacetylation is carried out by reacting the starting material with a tin compound of the formula R.sub.3 SnOR' where R and R' designate lower alkyl.
		The removal of the acetyl group at the anomeric position is a highly selective one when the reaction is effected in alkanols.
	www.freepatentsonline.com /4855417.html (2007 words)

	dec2.html
		Now the alcohol attacks this carbon because it is electropositive, to form the glycosidic bond.
		For the second sugar, we do the same: We indicate the configuration of the anomeric carbon, the series (D or L), and if it is a furanose or pyranose.
		This is because all the chains and braches finish in a sugar whose anomeric carbon is involved in the glycosidic bond.
	tonga.usip.edu /gmoyna/biochem341/lecture34.html (2729 words)

	Carbohydrates - Fructose
		The -OH on carbon #5 is converted into the ether linkage to close the ring with carbon #2.
		The anomeric carbon is the center of a hemiketal functional group.
		A carbon that has both an ether oxygen and an alcohol group (and is attached to two other carbons is a hemiketal.
	www.elmhurst.edu /~chm/vchembook/543fructose.html (556 words)

	Steve's place - Carbohydrates
		Numbering of carbons: C1 is the carbonyl carbon, C6 the furthest carbon from this.
		Carbon 1 is the anomeric carbon, and doesn't exist in the open chain form, so we're left with carbon 5 to understand.
		Glucose is in the α anomeric form (OH on carbon-1 is on the opposite side to the CH OH on carbon-5), and fructose is in the β anomeric form (OH on carbon-2 is on the same side as the CH OH on carbon-5).
	www.steve.gb.com /science/carbohydrates.html (2287 words)

	Anomeric fluororibosyl amines - Patent 5480992
		Anomeric 2,2-difluororibosyl azide and amine intermediates which are useful for the preparation of 2'-deoxynucleosides, and processes thereto, are provided.
		This invention relates to the fields of pharmaceutical and organic chemistry, and provides novel anomeric 2,2-difluororibosyl azide intermediates and 2,2-difluororibosyl amine intermediates, each of which is useful in the preparation of 2'-deoxy-2',2'-difluoronucleosides.
		Preferrably, the anomeric amine of formula I is in a protected form (when each R.sup.2 is a hydroxy protecting group) prior to the condensation step.
	www.freepatentsonline.com /5480992.html (3490 words)

	Anomeric Carbon Encyclopedia Article, History, Biography at Karr.net (Site not responding. Last check: 2007-10-06)
		Anomeric Carbon Encyclopedia Article, History, Biography at Karr.net
		Looking For anomeric carbon - Find anomeric carbon and more at Lycos Search.
		Find anomeric carbon - Your relevant result is a click away!
	www.karr.net /encyclopedia/Anomeric_carbon (191 words)

	2-Carb-6 and 2-Carb-7
		The new centre of chirality generated by hemiacetal ring closure is called the anomeric centre.
		anomer, the exocyclic oxygen atom at the anomeric centre is formally cis, in the Fischer projection, to the oxygen attached to the anomeric reference atom; in the
		In this case, the configuration of the anomeric carbon atom is indicated by the appropriate symbol R or S according to the sequence rule (cf.
	alpha.qmw.ac.uk /~ugca000/iupac2/2carb/06n07.html (914 words)

	GlycoWord / Saccharide-B01
		The anomeric configuration of the glycosyl linkage formed by transglycosylation is identical to that by hydrolysis, and in condensation it becomes the configuration of the substrate of hydrolysis.
		In the case of the retaining enzyme, the -COO- attacks the anomeric carbon atom with cooperative cleavage of the glucosyl linkage by -COOH (A in the figure).
		In the scheme for the inverting-type enzyme the structure of I is shown at the end of the reaction, which implies that the activation of the water molecule is done by -COO-, reversing the protonation of two carboxyl groups before and after hydrolysis (see G and J).
	www.glycoforum.gr.jp /science/word/saccharide/SA-B01E.html (907 words)

	2-Carb-6 and 2-Carb-7
		The anomeric reference atom is the configurational atom (see 2-Carb-4.2 and 2-Carb-4.3) of the parent, unless multiple configurational prefixes (see 2-Carb-8.3) are used.
		If multiple configurational prefixes are used, the anomeric reference atom is the highest-numbered atom of the group of chiral centres next to the anomeric centre that is involved in the heterocyclic ring and specified by a single configurational prefix.
		are applicable only when the anomeric carbon atom has a lower locant than the anomeric reference atom.
	www.chem.qmw.ac.uk /iupac/2carb/06n07.html (914 words)

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