72:
217:
224:
164:
157:
301:
287:
280:
294:
108:
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
429:
343:
reactions. Epimerization can be spontaneous (generally a slow process), or catalysed by enzymes, e.g. the epimerization between the sugars
340:
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
339:
Epimerization is a chemical process where an epimer is converted to its diastereomeric counterpart. It can happen in
71:
519:
110:
149:
are epimers that differ at the C-4 position, with the former being equatorial and the latter being axial.
43:
193:
In the case that the difference is the -OH groups on C-1, the anomeric carbon, such as in the case of α-
470:
Zhang, Chunming; Trudell, Mark L. (1996). "A Short and
Efficient Total Synthesis of (±)-Epibatidine".
216:
223:
351:
344:
47:
269:
368:
synthesis is an example of epimerization. Pharmaceutical examples include epimerization of the
495:
487:
479:
443:
408:
373:
134:
50:
out of at least two. All other stereogenic centers in the molecules are the same in each.
31:
513:
412:
97:
439:
163:
156:
385:
369:
254:
39:
376:
to the pharmacologically preferred and lower-energy threo isomers, and undesired
434:
381:
365:
300:
201:-glucopyranose, the molecules are both epimers and anomers (as indicated by the
57:
458:
114:
61:
491:
438:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
447:
146:
499:
286:
279:
261:
17:
293:
265:
105:
483:
130:
358:
54:
is the interconversion of one epimer to the other epimer.
419:(2nd ed.). Oxford University Press. p. 1112.
364:
The penultimate step in Zhang & Trudell's classic
117:. (Enantiomers have the same name, but differ in
137:involved in the stereochemistry. Similarly, β-
8:
403:
401:
129:classification.) They are also not sugar
64:are two epimers that are used as drugs.
274:
211:
151:
66:
397:
7:
253:Other closely related compounds are
435:Compendium of Chemical Terminology
341:condensed tannins depolymerization
25:
459:Structure of the glucose molecule
80:Doxorubicin–epirubicin comparison
472:The Journal of Organic Chemistry
299:
292:
285:
278:
222:
215:
162:
155:
70:
42:. The two epimers have opposite
27:One of a pair of diastereomers
1:
306:
229:
169:
77:
536:
357:, which is catalysed by
448:10.1351/goldbook.E02167
133:, since it is not the
359:renin-binding protein
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
332:
331:
250:
249:
244:
235:
200:
196:
190:
189:
184:
175:
144:
140:
127:
121:
103:
95:
85:
84:
16:(Redirected from
527:
504:
503:
467:
461:
456:
450:
427:
421:
420:
405:
303:
296:
289:
282:
275:
242:
233:
226:
219:
212:
198:
194:
182:
173:
166:
159:
152:
142:
138:
125:
119:
101:
93:
74:
67:
21:
535:
534:
530:
529:
528:
526:
525:
524:
520:Stereochemistry
510:
509:
508:
507:
469:
468:
464:
457:
453:
428:
424:
407:
406:
399:
394:
374:methylphenidate
370:erythro isomers
337:
328:
323:
318:
313:
252:
246:
237:
192:
186:
185:-mannopyranose
177:
176:-glucopyranose
147:galactopyranose
135:anomeric carbon
90:
81:
32:stereochemistry
28:
23:
22:
15:
12:
11:
5:
533:
531:
523:
522:
512:
511:
506:
505:
462:
451:
422:
413:Warren, Stuart
396:
395:
393:
390:
336:
333:
330:
329:
326:
324:
321:
319:
316:
314:
308:
305:
304:
297:
290:
283:
248:
247:
245:-glucopyranose
240:
238:
236:-glucopyranose
231:
228:
227:
220:
209:designation).
188:
187:
180:
178:
171:
168:
167:
160:
89:
86:
83:
82:
79:
76:
75:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
532:
521:
518:
517:
515:
501:
497:
493:
489:
485:
481:
477:
473:
466:
463:
460:
455:
452:
449:
445:
441:
437:
436:
431:
426:
423:
418:
414:
410:
404:
402:
398:
391:
389:
387:
383:
379:
375:
371:
367:
362:
360:
356:
354:
349:
347:
342:
335:Epimerization
334:
325:
320:
315:
311:
307:
302:
298:
295:
291:
288:
284:
281:
277:
276:
273:
271:
267:
263:
259:
257:
239:
230:
225:
221:
218:
214:
213:
210:
208:
204:
179:
170:
165:
161:
158:
154:
153:
150:
148:
136:
132:
128:
122:
116:
112:
107:
106:mannopyranose
99:
98:glucopyranose
87:
78:
73:
69:
68:
65:
63:
59:
55:
53:
52:Epimerization
49:
45:
44:configuration
41:
40:diastereomers
37:
33:
19:
475:
471:
465:
454:
433:
425:
416:
386:brasofensine
377:
363:
352:
345:
338:
309:
255:
251:
206:
202:
191:
124:
118:
91:
56:
51:
46:at only one
35:
29:
382:tesofensine
366:epibatidine
115:enantiomers
58:Doxorubicin
392:References
327:Epilipoxin
270:epilipoxin
62:epirubicin
492:0022-3263
312:-inositol
258:-inositol
18:Epimerize
514:Category
500:11667626
415:(2012).
317:Inositol
262:inositol
88:Examples
440:Epimers
378:in vivo
322:Lipoxin
266:lipoxin
131:anomers
498:
490:
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
123:and
60:and
480:doi
444:doi
442:".
384:to
372:of
310:epi
256:epi
30:In
516::
494:.
486:.
476:61
474:.
432:,
400:^
388:.
361:.
272:.
241:β-
232:α-
181:β-
172:β-
502:.
482::
446::
353:N
346:N
243:D
234:D
207:β
203:α
199:D
195:D
183:D
174:D
145:-
143:D
139:D
126:L
120:D
104:-
102:D
96:-
94:D
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.