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Wikipedia

Crotonyl-CoA

Crotonyl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.[1] It is important in the metabolism of fatty acids and amino acids.[2]

Crotonyl-CoA
Names
IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-4-({3-[(2-{[(2E)-but-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl (3R)-4-({3-[(2-{[(2E)-but-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
Identifiers
  • 992-67-6 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 444072
ECHA InfoCard 100.012.360
MeSH Crotonyl-coenzyme+A
  • 592
UNII
  • Q959BSX9OA Y
  • DTXSID30904345
  • InChI=1/C36H46N4O7S2/c1-25(2)24-40(49(45,46)30-19-15-27(4)16-20-30)34(36(42)47-5)12-8-9-21-37-35(41)33(22-28-23-38-32-11-7-6-10-31(28)32)39-48(43,44)29-17-13-26(3)14-18-29/h6-7,10-11,13-20,23,25,33-34,38-39H,8-9,12,21-22,24H2,1-5H3,(H,37,41)/t33-,34-/m0/s1
    Key: KDDJMRASDNUVJO-HEVIKAOCBM
  • O=S(=O)(c1ccc(cc1)C)N(CC(C)C)[C@H](C(=O)OC)CCCCNC(=O)[C@@H](NS(=O)(=O)c2ccc(cc2)C)Cc4c3ccccc3[nH]c4
Properties
C25H40N7O17P3S
Molar mass 835.609 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Crotonyl-coA and reductases edit

Before a 2007 report by Alber and coworkers, crotonyl-coA carboxylases and reductases (CCRs) were known for reducing crotonyl-coA to butyryl-coA.[3] A report by Alber and coworkers concluded that a specific CCR homolog was able to reduce crotonyl-coA to (2S)-ethyl malonyl-coA which was a favorable reaction.[3] The specific CCR homolog came from the bacterium Rhodobacter sphaeroides.[3]

Role of Crotonyl-coA in Transcription edit

Post-translational modification of histones either by acetylation or crotonylation is important for the active transcription of genes.[4] Histone crotonylation is regulated by the concentration of crotonyl-coA which can change based on environmental cell conditions or genetic factors.[4]

References edit

  1. ^ Ray, Lauren; Valentic, Timothy R; Miyazawa, Takeshi; Withall, David M; Song, Lijiang; Milligan, Jacob C; Osada, Hiroyuki; Takahashi, Shunji; Tsai, Shiou-Chuan; Challis, Gregory L (2016). "A crotonyl-CoA reductase-carboxylase independent pathway for assembly of unusual alkylmalonyl-CoA polyketide synthase extender units". Nature Communications. 7: 13609. Bibcode:2016NatCo...713609R. doi:10.1038/ncomms13609. PMC 5187497. PMID 28000660.
  2. ^ "Crotonyl-CoA".
  3. ^ a b c Wilson, Micheal C.; Moore, Bradley S. (2012). "Beyond ethylmalonyl-CoA: The functional role of crotonyl-CoAcarboxylase/reductase homologs in expanding polyketide diversity". Nat. Prod. Rep. 29 (1): 72–86. doi:10.1039/c1np00082a. ISSN 0265-0568. PMID 22124767.
  4. ^ a b Sabari, Benjamin R.; Tang, Zhanyun; Huang, He; Yong-Gonzalez, Vladimir; Molina, Henrik; Kong, Ha Eun; Dai, Lunzhi; Shimada, Miho; Cross, Justin R.; Zhao, Yingming; Roeder, Robert G. (2015-04-16). "Intracellular Crotonyl-CoA Stimulates Transcription through p300-Catalyzed Histone Crotonylation". Molecular Cell. 58 (2): 203–215. doi:10.1016/j.molcel.2015.02.029. ISSN 1097-2765. PMC 4501262. PMID 25818647.

See also edit


crotonyl, crotonyl, coenzyme, intermediate, fermentation, butyric, acid, metabolism, lysine, tryptophan, important, metabolism, fatty, acids, amino, acids, namesiupac, name, phosphonoadenosine, enoyl, sulfanyl, ethyl, amino, oxopropyl, amino, hydroxy, dimethyl. Crotonyl coenzyme A is an intermediate in the fermentation of butyric acid and in the metabolism of lysine and tryptophan 1 It is important in the metabolism of fatty acids and amino acids 2 Crotonyl CoA NamesIUPAC name 3 O Phosphonoadenosine 5 3R 4 3 2 2E but 2 enoyl sulfanyl ethyl amino 3 oxopropyl amino 3 hydroxy 2 2 dimethyl 4 oxobutyl dihydrogen diphosphate Systematic IUPAC name 2R 3S 4R 5R 5 6 Amino 9H purin 9 yl 4 hydroxy 3 phosphonooxy oxolan 2 yl methyl 3R 4 3 2 2E but 2 enoyl sulfanyl ethyl amino 3 oxopropyl amino 3 hydroxy 2 2 dimethyl 4 oxobutyl dihydrogen diphosphateIdentifiersCAS Number 992 67 6 Y3D model JSmol Interactive imageChemSpider 444072ECHA InfoCard 100 012 360MeSH Crotonyl coenzyme APubChem CID 592UNII Q959BSX9OA YCompTox Dashboard EPA DTXSID30904345InChI InChI 1 C36H46N4O7S2 c1 25 2 24 40 49 45 46 30 19 15 27 4 16 20 30 34 36 42 47 5 12 8 9 21 37 35 41 33 22 28 23 38 32 11 7 6 10 31 28 32 39 48 43 44 29 17 13 26 3 14 18 29 h6 7 10 11 13 20 23 25 33 34 38 39H 8 9 12 21 22 24H2 1 5H3 H 37 41 t33 34 m0 s1Key KDDJMRASDNUVJO HEVIKAOCBMSMILES O S O c1ccc cc1 C N CC C C C H C O OC CCCCNC O C H NS O O c2ccc cc2 C Cc4c3ccccc3 nH c4PropertiesChemical formula C25H40N7O17P3SMolar mass 835 609 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Crotonyl coA and reductases 2 Role of Crotonyl coA in Transcription 3 References 4 See alsoCrotonyl coA and reductases editBefore a 2007 report by Alber and coworkers crotonyl coA carboxylases and reductases CCRs were known for reducing crotonyl coA to butyryl coA 3 A report by Alber and coworkers concluded that a specific CCR homolog was able to reduce crotonyl coA to 2S ethyl malonyl coA which was a favorable reaction 3 The specific CCR homolog came from the bacterium Rhodobacter sphaeroides 3 Role of Crotonyl coA in Transcription editPost translational modification of histones either by acetylation or crotonylation is important for the active transcription of genes 4 Histone crotonylation is regulated by the concentration of crotonyl coA which can change based on environmental cell conditions or genetic factors 4 References edit Ray Lauren Valentic Timothy R Miyazawa Takeshi Withall David M Song Lijiang Milligan Jacob C Osada Hiroyuki Takahashi Shunji Tsai Shiou Chuan Challis Gregory L 2016 A crotonyl CoA reductase carboxylase independent pathway for assembly of unusual alkylmalonyl CoA polyketide synthase extender units Nature Communications 7 13609 Bibcode 2016NatCo 713609R doi 10 1038 ncomms13609 PMC 5187497 PMID 28000660 Crotonyl CoA a b c Wilson Micheal C Moore Bradley S 2012 Beyond ethylmalonyl CoA The functional role of crotonyl CoAcarboxylase reductase homologs in expanding polyketide diversity Nat Prod Rep 29 1 72 86 doi 10 1039 c1np00082a ISSN 0265 0568 PMID 22124767 a b Sabari Benjamin R Tang Zhanyun Huang He Yong Gonzalez Vladimir Molina Henrik Kong Ha Eun Dai Lunzhi Shimada Miho Cross Justin R Zhao Yingming Roeder Robert G 2015 04 16 Intracellular Crotonyl CoA Stimulates Transcription through p300 Catalyzed Histone Crotonylation Molecular Cell 58 2 203 215 doi 10 1016 j molcel 2015 02 029 ISSN 1097 2765 PMC 4501262 PMID 25818647 See also editCrotonic acid Glutaryl CoA dehydrogenase nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Crotonyl CoA amp oldid 1152487811, wikipedia, wiki, book, books, library,

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