22:
246:
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.
120:
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.
226:
665:
663:
Balser, Klaus; Hoppe, Lutz; Eicher, Theo; Wandel, Martin; Astheimer, Hans‐Joachim; Steinmeier, Hans; Allen, John M. (2004). "Cellulose Esters".
634:
86:
Deacylations "play crucial roles in gene transcription and most likely in all eukaryotic biological processes that involve chromatin".
412:
Bolden, Jessica E.; Peart, Melissa J.; Johnstone, Ricky W. (2006). "Anticancer activities of histone deacetylase inhibitors".
682:
648:
98:
158:. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable.
455:
Shahbazian, Mona D.; Grunstein, Michael (2007). "Functions of Site-Specific
Histone Acetylation and Deacetylation".
194:
90:
715:
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110:
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as a catalyst. This methodology allows the preparation of enantio-enriched alcohols and acetates.
134:
133:
are generally prepared by acetylations. Acetylations are often used in making C-acetyl bonds in
468:
8:
114:
437:
389:
364:
340:
315:
164:. At one time acetic anhydride was prepared by the reaction of ketene with acetic acid:
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is the opposite reaction, the removal of an acetyl group from a chemical compound.
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365:"Lysine Acetylation Goes Global: From Epigenetics to Metabolism and Therapeutics"
155:
102:
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331:
46:
25:
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707:
619:
590:
560:
530:
503:
272:
256:
604:
Denoon, C. E. Jr.; Adkins, Homer; Rainey, James L. (1940). "Acetylacetone".
152:. This reagent is common in the laboratory; its use cogenerates acetic acid.
476:
433:
398:
349:
54:
50:
490:
F. K. Thayer (1925). "Acetylmandelic Acid and
Acetylmandelyl Chloride".
577:
Merritt, Jr., Charles; Braun, Charles E. (1950). "9-Acetylanthracene".
640:
277:
130:
38:
636:
425:
137:. Carbanions and their equivalents are susceptible to acetylations.
97:, which is common, converts a charged side chain to a neutral one.
21:
363:
Ali, Ibraheem; Conrad, Ryan J.; Verdin, Eric; Ott, Melanie (2018).
546:
316:"Erasers of Histone Acetylation: The Histone Deacetylase Enzymes"
70:
29:
547:
F. E. Ray and George
Rieveschl, Jr (1948). "2-Acetylfluorene".
260:
243:
161:
106:
94:
287:
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64:
16:
Chemical reaction that attaches an acetyl group to a compound
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Many acetylations are achieved using these three reagents:
662:
81:
109:. These modifications are effected by enzymes called
93:
of proteins. The acetylation of the ε-amino group of
197:
411:
517:Herbst, R. M.; Shemin, D. (1939). "Acetylglycine".
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603:
362:
220:
576:
728:
542:
540:
700:Encyclopedia of Reagents for Organic Synthesis
666:Ullmann's Encyclopedia of Industrial Chemistry
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698:Manchand, Percy S. (2001). "Vinyl Acetate".
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221:{\displaystyle \Delta H=-63{\text{ kJ/mol}}}
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320:Cold Spring Harbor Perspectives in Biology
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469:10.1146/annurev.biochem.76.052705.162114
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639:(in German) (6th ed.), Weinheim:
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99:Acetylation/deacetylation of histones
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82:Acetylation/deacetylation in biology
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14:
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91:post-translational modification
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448:
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314:Seto, E.; Yoshida, M. (2014).
1:
675:10.1002/14356007.a05_419.pub2
457:Annual Review of Biochemistry
414:Nature Reviews Drug Discovery
298:
61:. Such compounds are termed
7:
381:10.1021/acs.chemrev.7b00181
332:10.1101/cshperspect.a018713
266:
89:Acetylation is one type of
10:
753:
633:Arpe, Hans-Jürgen (2007),
235:
111:histone acetyltransferases
708:10.1002/047084289X.rv008
620:10.15227/orgsyn.020.0006
591:10.15227/orgsyn.030.0001
561:10.15227/orgsyn.028.0003
531:10.15227/orgsyn.019.0004
504:10.15227/orgsyn.004.0001
232:Acetylation of cellulose
135:Friedel-Crafts reactions
669:. Weinheim: Wiley-VCH.
259:as an acetyl donor and
255:Transacetylation uses
222:
32:
28:is acetylated to form
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101:also plays a role in
24:
195:
141:Acetylation reagents
115:histone deacetylases
129:Acetate esters and
53:. It introduces an
643:, pp. 200–1,
218:
33:
737:Organic reactions
684:978-3-527-30385-4
650:978-3-527-31540-6
607:Organic Syntheses
579:Organic Syntheses
549:Organic Syntheses
519:Organic Syntheses
492:Organic Syntheses
293:Organic synthesis
238:Cellulose acetate
216:
125:Organic synthesis
59:chemical compound
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375:(3): 1216–1252.
369:Chemical Reviews
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251:Transacetylation
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150:Acetic anhydride
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242:Cellulose is a
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156:Acetyl chloride
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103:gene expression
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49:reaction with
47:esterification
45:is an organic
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26:Salicylic acid
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273:Acetoxy group
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257:vinyl acetate
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76:Deacetylation
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215: kJ/mol
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62:
55:acetyl group
42:
36:
113:(HATs) and
51:acetic acid
43:acetylation
717:0471936235
463:: 75–100.
299:References
236:See also:
174:C=C=O + CH
131:acetamides
117:(HDACs).
68:or simply
641:Wiley-VCH
278:Acylation
208:−
199:Δ
182:H → (CH
39:chemistry
731:Category
477:17362198
434:16955068
399:29405707
350:24691964
267:See also
71:acetates
63:acetate
442:2857250
390:6609103
341:3970420
57:into a
30:aspirin
714:
681:
647:
475:
440:
432:
397:
387:
348:
338:
261:lipase
244:polyol
162:Ketene
107:cancer
95:lysine
65:esters
614:: 6.
585:: 1.
555:: 3.
525:: 4.
498:: 1.
438:S2CID
288:Ester
283:Amide
712:ISBN
679:ISBN
645:ISBN
473:PMID
430:PMID
395:PMID
346:PMID
105:and
704:doi
671:doi
616:doi
587:doi
557:doi
527:doi
500:doi
465:doi
422:doi
385:PMC
377:doi
373:118
336:PMC
328:doi
186:CO)
37:In
733::
710:.
702:.
677:.
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610:.
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581:.
569:^
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459:.
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306:^
211:63
178:CO
74:.
41:,
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479:.
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418:5
401:.
379::
352:.
330::
324:6
205:=
202:H
190:O
188:2
184:3
180:2
176:3
172:2
170:H
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