Cas no 2140-48-9 (Coenzyme A, S-butanoate)

Coenzyme A, S-butanoate structure
Coenzyme A, S-butanoate structure
Product Name:Coenzyme A, S-butanoate
CAS No:2140-48-9
MF:C25H42N7O17P3S
MW:837.623967647552
CID:261027
PubChem ID:122283
Update Time:2025-04-19

Coenzyme A, S-butanoate Chemical and Physical Properties

Names and Identifiers

    • Coenzyme A, S-butanoate
    • [5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-butanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosph
    • [5-(6-aminopurin-9-yl)-2-[[[[3-[2-(2-butanoylsulfanylethylcarbamoyl)ethylcarbamoyl]-3-hydroxy-2,2-dimethyl-propoxy]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid
    • butanoyl-CoA
    • Butyryl-CoA
    • butyrylcoenzyme A
    • S-butyryl-coenzyme-A
    • n-Butyryl-CoA
    • Butyryl coenzyme A
    • Butyryl CoA
    • Butanoyl-CoA
    • Butanoyl coenzyme A
    • Coenzyme A, S-butyrate (6CI,7CI,8CI)
    • Butyryl Coenzyme A (sodium salt)
    • C4:0-CoA
    • 2140-48-9
    • S-Butyryl-coenzym-A
    • S-butanoyl-coenzyme A
    • S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] butanethioate
    • ranosyl]-
    • Coenzyme A, butyryl-
    • butyryl-CoA; (Acyl-CoA); [M+H]+;
    • 9H-purin-6-amine,9-[5-O-[hydroxy[[hydroxy[[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[[2-[(1-oxobutyl)thio]ethyl]amino]propyl]amino]butyl]oxy]phosphinyl]oxy]phosphinyl]-3-O-phosphono-beta-D-ribofu
    • DTXSID70943955
    • S-butanoyl-CoA
    • S-butyryl-coenzyme A
    • butanoyl-coenzyme A
    • 4:0-CoA
    • LMFA07050292
    • Butyryl CoA
    • 'Butyryl Coenzyme A'
    • Butyryl coenzyme A
    • S-butyryl-CoA
    • Butanoyl coenzyme A
    • C00136
    • 3'-phosphoadenosine 5'-(3-{(3R)-4-[(3-{[2-(butanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate)
    • BCO
    • butyryl-coenzyme A
    • SCHEMBL60439
    • CHEBI:15517
    • n-Butyryl-CoA
    • S-{(3S,5S,9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~-diphosphaheptadecan-17-yl} butanethioate (non-preferred name)
    • S-{1-[5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14-tetraoxo-2,4,6-trioxa-11,15-diaza-3lambda5,5lambda5-diphosphaheptadecan-17-yl} butanethioate
    • NS00014819
    • SCHEMBL4367366
    • DTXSID70862839
    • S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] butanethioate
    • Q42412398
    • butyryl-coenzyme A(4-)
    • butanoyl-coenzyme A(4-)
    • butyryl-coenzyme A tetraanion
    • Inchi： 1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,18-,19-,20+,24-/m1/s1
    • InChI Key： CRFNGMNYKDXRTN-CITAKDKDSA-N
    • SMILES： S(C(CCC)=O)CCNC(CCNC([C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3C(N)=NC=NC2=3)O1)O)OP(=O)(O)O)O)=O)=O

Computed Properties

  • Exact Mass: 901.13700
  • Monoisotopic Mass: 837.157073
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 9
  • Hydrogen Bond Acceptor Count: 18
  • Heavy Atom Count: 53
  • Rotatable Bond Count: 22
  • Complexity: 1410
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: _4.8
  • Topological Polar Surface Area: 389

Experimental Properties

  • Density: 1.83
  • Boiling Point: °Cat760mmHg
  • Flash Point: °C
  • Refractive Index: 1.7
  • PSA: 455.28000
  • LogP: 0.55420

Coenzyme A, S-butanoate Production Method

Production Method 1

Reaction Conditions
1.1R:PyBOP, R:K2CO3, S:H2O, S:THF, 2 h, rt
2.1R:Codehydrase I, S:H2O, overnight, 37°C, pH 7.5
Reference
Extending Carbon Chain Length of 1-Butanol Pathway for 1-Hexanol Synthesis from Glucose by Engineered Escherichia coli
By Dekishima, Yasumasa et al, Journal of the American Chemical Society, 2011, 133(30), 11399-11401

Production Method 2

Reaction Conditions
1.1R:R:R:S:H2O
Reference
6-Deoxyerythronolide B Analogue Production in Escherichia coli through Metabolic Pathway Engineering
By Kennedy, Jonathan et al, Biochemistry, 2003, 42(48), 14342-14348

Production Method 3

Reaction Conditions
1.1
Reference
Rational Control of Polyketide Extender Units by Structure-Based Engineering of a Crotonyl-CoA Carboxylase/Reductase in Antimycin Biosynthesis
By Zhang, Lihan et al, Angewandte Chemie, 2015, 54(45), 13462-13465

Production Method 4

Reaction Conditions
1.1R:NaHCO3, S:H2O, 20 min, cooled
Reference
Covalent Adduct Formation as a Strategy for Efficient CO2 Fixation in Crotonyl-CoA Carboxylases/Reductases
By Recabarren, Rodrigo et al, ACS Catalysis, 2023, 13(9), 6230-6241

Production Method 5

Reaction Conditions
1.1R:K2HPO4, R:KH2PO4, C:227465-96-5, 3 h, 37°C, pH 7
Reference
Enzymatic preparation technique for acyl/aroyl coenzyme a
By Zhu, Ping et al, PCT Int. Appl., From PCT Int. Appl., 2022228297, 03 Nov 2022, 2022228297, 03 Nov 2022

Production Method 6

Reaction Conditions
1.1R:MgCl2, C:9013-18-7, C:Cleland's reagent, C:34369-07-8, C:Ortho-Gynol, S:H2O, 2 h, 30°C, pH 8
1.2R:CHCl3
Reference
Identification of an α-Oxoamine Synthase and a One-Pot Two-Step Enzymatic Synthesis of α-Amino Ketones
By Zhou, Ting et al, Organic Letters, 2021, 23(1), 37-41

Production Method 7

Reaction Conditions
1.1R:Coenzyme II, C:93389-35-6
2.1C:9027-46-7
3.1R:Coenzyme II, reduced, C:9028-40-4, C:39319-78-3
4.1C:9027-13-8
5.1R:Coenzyme II, reduced, C:9027-88-7
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 8

Reaction Conditions
1.1R:Coenzyme II, reduced, C:9075-02-9, C:9024-32-2
2.1R:Coenzyme II, C:37211-61-3, C:9082-72-8
3.1C:116405-23-3
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 9

Reaction Conditions
1.1C:9027-46-7
2.1R:Coenzyme II, reduced, C:9028-40-4, C:39319-78-3
3.1C:9027-13-8
4.1R:Coenzyme II, reduced, C:9027-88-7
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 10

Reaction Conditions
1.1R:Coenzyme II, reduced, C:9028-40-4, C:39319-78-3
2.1C:9027-13-8
3.1R:Coenzyme II, reduced, C:9027-88-7
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 11

Reaction Conditions
1.1R:Coenzyme II, C:37211-61-3, C:9082-72-8
2.1C:116405-23-3
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 12

Reaction Conditions
1.1C:9027-13-8
2.1R:Coenzyme II, reduced, C:9027-88-7
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 13

Reaction Conditions
1.1R:MgCl2, R:R:Coenzyme II, reduced, R:NaHCO3, C:9023-95-4, C:37251-07-3, S:H2O, 1 h, rt, pH 8.0
1.2R:Cl3CCO2H, S:H2O
Reference
Enzymatic Synthesis of Dilactone Scaffold of Antimycins
By Sandy, Moriah et al, ACS Chemical Biology, 2012, 7(12), 1956-1961

Production Method 14

Reaction Conditions
1.1S:H2O, 72 h, 37°C
Reference
Metabolic engineering of Clostridium acetobutylicum for the production of butyl butyrate
By Noh, Hyeon Ji et al, Applied Microbiology and Biotechnology, 2018, 102(19), 8319-8327

Production Method 15

Reaction Conditions
1.1R:R:KH2PO4, C:227465-96-5, 3 h, 37°C, pH 7
Reference
Enzymatic preparation technique for acyl/aroyl coenzyme a
By Zhu, Ping et al, Faming Zhuanli Shenqing, From Faming Zhuanli Shenqing, 115247192, 28 Oct 2022, 115247192, 28 Oct 2022

Production Method 16

Reaction Conditions
1.1R:Coenzyme II, C:9001-60-9, C:9028-36-8
2.1C:9027-45-6
3.1R:Coenzyme II, reduced, C:9075-02-9, C:9024-32-2
4.1R:Coenzyme II, C:37211-61-3, C:9082-72-8
5.1C:116405-23-3
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 17

Reaction Conditions
1.1C:116405-23-3
Reference
In-vitro enzymatic butanol production
By Garibay Orijel, Claudio et al, PCT Int. Appl., From PCT Int. Appl., 2017191483, 09 Nov 2017, 2017191483, 09 Nov 2017

Production Method 18

Reaction Conditions
1.1R:R:MgCl2, R:Glycerol, R:C:9013-18-7, S:H2O, 60 min, 25°C
1.2R:HCO2H
Reference
Identification of Middle Chain Fatty Acyl-CoA Ligase Responsible for the Biosynthesis of 2-Alkylmalonyl-CoAs for Polyketide Extender Unit
By Miyazawa, Takeshi et al, Journal of Biological Chemistry, 2015, 290(45), 26994-27011

Production Method 19

Reaction Conditions
1.1C:9027-46-7, S:H2O, 60°C, pH 7.5
2.1R:C:9028-40-4, S:H2O, 60°C, pH 7.5
3.1C:9027-13-8, S:H2O, 60°C, pH 7.5
4.1R:C:77649-64-0, S:H2O, 60°C, pH 7.5
Reference
A hybrid synthetic pathway for butanol production by a hyperthermophilic microbe
By Keller, Matthew W. et al, Metabolic Engineering, 2015, 27, 101-106

Production Method 20

Reaction Conditions
1.1R:C:9028-40-4, S:H2O, 60°C, pH 7.5
2.1C:9027-13-8, S:H2O, 60°C, pH 7.5
3.1R:C:77649-64-0, S:H2O, 60°C, pH 7.5
Reference
A hybrid synthetic pathway for butanol production by a hyperthermophilic microbe
By Keller, Matthew W. et al, Metabolic Engineering, 2015, 27, 101-106

Production Method 21

Reaction Conditions
1.1C:9027-13-8, S:H2O, 60°C, pH 7.5
2.1R:C:77649-64-0, S:H2O, 60°C, pH 7.5
Reference
A hybrid synthetic pathway for butanol production by a hyperthermophilic microbe
By Keller, Matthew W. et al, Metabolic Engineering, 2015, 27, 101-106

Production Method 22

Reaction Conditions
1.1R:C:77649-64-0, S:H2O, 60°C, pH 7.5
Reference
A hybrid synthetic pathway for butanol production by a hyperthermophilic microbe
By Keller, Matthew W. et al, Metabolic Engineering, 2015, 27, 101-106

Production Method 23

Reaction Conditions
1.1S:H2O, cooled, pH 8
1.2R:HCl, S:H2O, pH 5
Reference
Identification of 3-sulfinopropionyl coenzyme A (CoA) desulfinases within the acyl-CoA dehydrogenase superfamily
By Schuermann, Marc et al, Journal of Bacteriology, 2014, 882-893, 13 pp.

Production Method 24

Reaction Conditions
1.1R:SOCl2, 3 h, reflux
2.1S:THF, 24 h, rt
3.1R:NaI, S:Me2CO, 24 h, rt
4.1R:NaOH, S:H2O, 24 h, rt, pH 9
4.2R:HCl, S:H2O, rt, pH 2
Reference
Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium
By Pal, Mohan and Bearne, Stephen L., Organic & Biomolecular Chemistry, 2014, 12(48), 9760-9763

Production Method 25

Reaction Conditions
1.1S:THF, 24 h, rt
2.1R:NaI, S:Me2CO, 24 h, rt
3.1R:NaOH, S:H2O, 24 h, rt, pH 9
3.2R:HCl, S:H2O, rt, pH 2
Reference
Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium
By Pal, Mohan and Bearne, Stephen L., Organic & Biomolecular Chemistry, 2014, 12(48), 9760-9763

Production Method 26

Reaction Conditions
1.1R:NaI, S:Me2CO, 24 h, rt
2.1R:NaOH, S:H2O, 24 h, rt, pH 9
2.2R:HCl, S:H2O, rt, pH 2
Reference
Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium
By Pal, Mohan and Bearne, Stephen L., Organic & Biomolecular Chemistry, 2014, 12(48), 9760-9763

Production Method 27

Reaction Conditions
1.1R:NaOH, S:H2O, 24 h, rt, pH 9
1.2R:HCl, S:H2O, rt, pH 2
Reference
Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium
By Pal, Mohan and Bearne, Stephen L., Organic & Biomolecular Chemistry, 2014, 12(48), 9760-9763

Production Method 28

Reaction Conditions
1.1R:C:77649-64-0
Reference
Biochemical and Structural Characterization of the trans-Enoyl-CoA Reductase from Treponema denticola
By Bond-Watts, Brooks B. et al, Biochemistry, 2012, 51(34), 6827-6837

Production Method 29

Reaction Conditions
1.1
Reference
Bacterial Acyl-CoA Mutase Specifically Catalyzes Coenzyme B12-dependent Isomerization of 2-Hydroxyisobutyryl-CoA and (S)-3-Hydroxybutyryl-CoA
By Yaneva, Nadya et al, Journal of Biological Chemistry, 2012, 287(19), 15502-15511

Coenzyme A, S-butanoate Raw materials

Coenzyme A, S-butanoate Preparation Products

Coenzyme A, S-butanoate Related Literature

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