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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
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reactions. Epimerization can be spontaneous (generally a slow process), or catalysed by enzymes, e.g. the epimerization between the sugars
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113:(up from the "plane" of the ring). These two molecules are epimers but, because they are not mirror images of each other, are not
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Epimerization is a chemical process where an epimer is converted to its diastereomeric counterpart. It can happen in
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are epimers that differ at the C-4 position, with the former being equatorial and the latter being axial.
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In the case that the difference is the -OH groups on C-1, the anomeric carbon, such as in the case of α-
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Zhang, Chunming; Trudell, Mark L. (1996). "A Short and
Efficient Total Synthesis of (±)-Epibatidine".
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synthesis is an example of epimerization. Pharmaceutical examples include epimerization of the
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out of at least two. All other stereogenic centers in the molecules are the same in each.
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to the pharmacologically preferred and lower-energy threo isomers, and undesired
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201:-glucopyranose, the molecules are both epimers and anomers (as indicated by the
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is the interconversion of one epimer to the other epimer.
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The penultimate step in Zhang & Trudell's classic
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137:involved in the stereochemistry. Similarly, β-
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129:classification.) They are also not sugar
64:are two epimers that are used as drugs.
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253:Other closely related compounds are
435:Compendium of Chemical Terminology
341:condensed tannins depolymerization
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459:Structure of the glucose molecule
80:Doxorubicin–epirubicin comparison
472:The Journal of Organic Chemistry
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42:. The two epimers have opposite
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197:-glucopyranose and β-
141:-glucopyranose and β-
92:The stereoisomers β-
38:is one of a pair of
355:-acetylmannosamine
348:-acetylglucosamine
48:stereogenic center
484:10.1021/jo9608681
478:(20): 7189–7191.
417:Organic Chemistry
411:; Greeves, Nick;
409:Clayden, Jonathan
380:epimerization of
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185:-mannopyranose
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52:Epimerization
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40:diastereomers
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18:Epimerization
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46:at only one
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382:tesofensine
366:epibatidine
115:enantiomers
58:Doxorubicin
392:References
327:Epilipoxin
270:epilipoxin
62:epirubicin
492:0022-3263
312:-inositol
258:-inositol
514:Category
500:11667626
415:(2012).
317:Inositol
262:inositol
88:Examples
440:Epimers
378:in vivo
322:Lipoxin
266:lipoxin
131:anomers
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100:and β-
36:epimer
430:IUPAC
111:axial
34:, an
496:PMID
488:ISSN
350:and
268:and
264:and
260:and
205:and
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384:to
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310:epi
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234:D
207:β
203:α
199:D
195:D
183:D
174:D
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143:D
139:D
126:L
120:D
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102:D
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