33:
257:
and thus susceptible to acetylation, which is achieved using acetic anhydride. Acetylation disrupts hydrogen bonding, which otherwise dominates the properties of cellulose. Consequently, the cellulose esters are soluble in organic solvents and can be cast into fibers and films.
131:
Two general mechanisms are known for deacetylation. One mechanism involves zinc binding to the acetyl oxygen. Another family of deacetylases require NAD, which transfers an ribosyl group to the acetyl oxygen.
237:
676:
674:
Balser, Klaus; Hoppe, Lutz; Eicher, Theo; Wandel, Martin; Astheimer, Hans‐Joachim; Steinmeier, Hans; Allen, John M. (2004). "Cellulose Esters".
645:
693:
659:
109:
97:
Deacylations "play crucial roles in gene transcription and most likely in all eukaryotic biological processes that involve chromatin".
101:
423:
Bolden, Jessica E.; Peart, Melissa J.; Johnstone, Ricky W. (2006). "Anticancer activities of histone deacetylase inhibitors".
726:
169:. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable.
466:
Shahbazian, Mona D.; Grunstein, Michael (2007). "Functions of Site-Specific
Histone Acetylation and Deacetylation".
747:
205:
121:
145:
274:
as a catalyst. This methodology allows the preparation of enantio-enriched alcohols and acetates.
125:
448:
144:
are generally prepared by acetylations. Acetylations are often used in making C-acetyl bonds in
722:
689:
655:
617:
483:
440:
405:
356:
303:
248:
69:
479:
714:
681:
626:
597:
567:
537:
510:
475:
432:
395:
387:
346:
338:
160:
166:
113:
400:
375:
351:
326:
175:. At one time acetic anhydride was prepared by the reaction of ketene with acetic acid:
57:
36:
741:
283:
267:
452:
89:
is the opposite reaction, the removal of an acetyl group from a chemical compound.
65:
685:
376:"Lysine Acetylation Goes Global: From Epigenetics to Metabolism and Therapeutics"
391:
342:
61:
32:
718:
630:
601:
571:
541:
514:
17:
651:
615:
Denoon, C. E. Jr.; Adkins, Homer; Rainey, James L. (1940). "Acetylacetone".
288:
163:. This reagent is common in the laboratory; its use cogenerates acetic acid.
141:
49:
487:
444:
409:
360:
501:
F. K. Thayer (1925). "Acetylmandelic Acid and
Acetylmandelyl Chloride".
588:
Merritt, Jr., Charles; Braun, Charles E. (1950). "9-Acetylanthracene".
81:
40:
271:
254:
172:
117:
105:
647:
436:
148:. Carbanions and their equivalents are susceptible to acetylations.
108:, which is common, converts a charged side chain to a neutral one.
374:
Ali, Ibraheem; Conrad, Ryan J.; Verdin, Eric; Ott, Melanie (2018).
298:
293:
75:
327:"Erasers of Histone Acetylation: The Histone Deacetylase Enzymes"
558:
F. E. Ray and George
Rieveschl, Jr (1948). "2-Acetylfluorene".
27:
Chemical reaction that attaches an acetyl group to a compound
156:
Many acetylations are achieved using these three reagents:
120:. These modifications are effected by enzymes called
104:
of proteins. The acetylation of the ε-amino group of
208:
528:Herbst, R. M.; Shemin, D. (1939). "Acetylglycine".
231:
553:
551:
711:Encyclopedia of Reagents for Organic Synthesis
677:Ullmann's Encyclopedia of Industrial Chemistry
8:
709:Manchand, Percy S. (2001). "Vinyl Acetate".
232:{\displaystyle \Delta H=-63{\text{ kJ/mol}}}
331:Cold Spring Harbor Perspectives in Biology
399:
350:
320:
318:
224:
207:
583:
581:
480:10.1146/annurev.biochem.76.052705.162114
198:
194:
190:
186:
182:
31:
314:
650:(in German) (6th ed.), Weinheim:
110:Acetylation/deacetylation of histones
7:
93:Acetylation/deacetylation in biology
209:
25:
102:post-translational modification
325:Seto, E.; Yoshida, M. (2014).
1:
686:10.1002/14356007.a05_419.pub2
468:Annual Review of Biochemistry
425:Nature Reviews Drug Discovery
72:. Such compounds are termed
392:10.1021/acs.chemrev.7b00181
343:10.1101/cshperspect.a018713
100:Acetylation is one type of
764:
644:Arpe, Hans-Jürgen (2007),
246:
122:histone acetyltransferases
719:10.1002/047084289X.rv008
631:10.15227/orgsyn.020.0006
602:10.15227/orgsyn.030.0001
572:10.15227/orgsyn.028.0003
542:10.15227/orgsyn.019.0004
515:10.15227/orgsyn.004.0001
243:Acetylation of cellulose
146:Friedel-Crafts reactions
680:. Weinheim: Wiley-VCH.
270:as an acetyl donor and
266:Transacetylation uses
233:
43:
39:is acetylated to form
234:
112:also plays a role in
35:
206:
152:Acetylation reagents
126:histone deacetylases
140:Acetate esters and
64:. It introduces an
654:, pp. 200–1,
229:
44:
748:Organic reactions
695:978-3-527-30385-4
661:978-3-527-31540-6
618:Organic Syntheses
590:Organic Syntheses
560:Organic Syntheses
530:Organic Syntheses
503:Organic Syntheses
304:Organic synthesis
249:Cellulose acetate
227:
136:Organic synthesis
70:chemical compound
16:(Redirected from
755:
733:
732:
706:
700:
699:
671:
665:
664:
641:
635:
633:
612:
606:
605:
585:
576:
575:
555:
546:
545:
525:
519:
518:
498:
492:
491:
463:
457:
456:
420:
414:
413:
403:
386:(3): 1216–1252.
380:Chemical Reviews
371:
365:
364:
354:
322:
262:Transacetylation
238:
236:
235:
230:
228:
225:
202:
161:Acetic anhydride
21:
763:
762:
758:
757:
756:
754:
753:
752:
738:
737:
736:
729:
708:
707:
703:
696:
673:
672:
668:
662:
643:
642:
638:
614:
613:
609:
587:
586:
579:
557:
556:
549:
527:
526:
522:
500:
499:
495:
465:
464:
460:
437:10.1038/nrd2133
422:
421:
417:
373:
372:
368:
324:
323:
316:
312:
280:
264:
253:Cellulose is a
251:
245:
204:
203:
200:
196:
192:
188:
184:
180:
167:Acetyl chloride
154:
138:
114:gene expression
95:
28:
23:
22:
15:
12:
11:
5:
761:
759:
751:
750:
740:
739:
735:
734:
727:
701:
694:
666:
660:
636:
607:
577:
547:
520:
493:
458:
431:(9): 769–784.
415:
366:
337:(4): a018713.
313:
311:
308:
307:
306:
301:
296:
291:
286:
279:
276:
263:
260:
244:
241:
240:
239:
223:
220:
217:
214:
211:
177:
176:
170:
164:
153:
150:
137:
134:
94:
91:
60:reaction with
58:esterification
56:is an organic
46:
45:
37:Salicylic acid
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
760:
749:
746:
745:
743:
730:
724:
720:
716:
712:
705:
702:
697:
691:
687:
683:
679:
678:
670:
667:
663:
657:
653:
649:
648:
640:
637:
632:
628:
624:
620:
619:
611:
608:
603:
599:
595:
591:
584:
582:
578:
573:
569:
565:
561:
554:
552:
548:
543:
539:
535:
531:
524:
521:
516:
512:
508:
504:
497:
494:
489:
485:
481:
477:
473:
469:
462:
459:
454:
450:
446:
442:
438:
434:
430:
426:
419:
416:
411:
407:
402:
397:
393:
389:
385:
381:
377:
370:
367:
362:
358:
353:
348:
344:
340:
336:
332:
328:
321:
319:
315:
309:
305:
302:
300:
297:
295:
292:
290:
287:
285:
284:Acetoxy group
282:
281:
277:
275:
273:
269:
268:vinyl acetate
261:
259:
256:
250:
242:
221:
218:
215:
212:
179:
178:
174:
171:
168:
165:
162:
159:
158:
157:
151:
149:
147:
143:
135:
133:
129:
127:
123:
119:
115:
111:
107:
103:
98:
92:
90:
88:
87:Deacetylation
84:
83:
78:
77:
71:
67:
63:
59:
55:
51:
42:
38:
34:
30:
29:
19:
18:Deacetylation
710:
704:
675:
669:
646:
639:
622:
616:
610:
593:
589:
563:
559:
533:
529:
523:
506:
502:
496:
471:
467:
461:
428:
424:
418:
383:
379:
369:
334:
330:
265:
252:
226: kJ/mol
155:
139:
130:
99:
96:
86:
80:
73:
66:acetyl group
53:
47:
124:(HATs) and
62:acetic acid
54:acetylation
728:0471936235
474:: 75–100.
310:References
247:See also:
185:C=C=O + CH
142:acetamides
128:(HDACs).
79:or simply
652:Wiley-VCH
289:Acylation
219:−
210:Δ
193:H → (CH
50:chemistry
742:Category
488:17362198
445:16955068
410:29405707
361:24691964
278:See also
82:acetates
74:acetate
453:2857250
401:6609103
352:3970420
68:into a
41:aspirin
725:
692:
658:
486:
451:
443:
408:
398:
359:
349:
272:lipase
255:polyol
173:Ketene
118:cancer
106:lysine
76:esters
625:: 6.
596:: 1.
566:: 3.
536:: 4.
509:: 1.
449:S2CID
299:Ester
294:Amide
723:ISBN
690:ISBN
656:ISBN
484:PMID
441:PMID
406:PMID
357:PMID
116:and
715:doi
682:doi
627:doi
598:doi
568:doi
538:doi
511:doi
476:doi
433:doi
396:PMC
388:doi
384:118
347:PMC
339:doi
197:CO)
48:In
744::
721:.
713:.
688:.
623:20
621:.
594:30
592:.
580:^
564:28
562:.
550:^
534:19
532:.
505:.
482:.
472:76
470:.
447:.
439:.
427:.
404:.
394:.
382:.
378:.
355:.
345:.
333:.
329:.
317:^
222:63
189:CO
85:.
52:,
731:.
717::
698:.
684::
634:.
629::
604:.
600::
574:.
570::
544:.
540::
517:.
513::
507:4
490:.
478::
455:.
435::
429:5
412:.
390::
363:.
341::
335:6
216:=
213:H
201:O
199:2
195:3
191:2
187:3
183:2
181:H
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
