Cas no 1264-45-5 (Coenzyme A, S-(hydrogen 2-methylpropanedioate))

Coenzyme A, S-(hydrogen 2-methylpropanedioate), is a modified coenzyme A derivative where the thiol group is esterified with hydrogen 2-methylpropanedioate. This compound is of interest in biochemical and enzymatic research due to its potential role as a substrate analog or inhibitor in metabolic pathways involving CoA-dependent enzymes. The 2-methylpropanedioate moiety introduces structural variability, which may influence binding affinity or reactivity in specific enzymatic contexts. This derivative is particularly useful for studying acyl-CoA synthetases, transferases, or other CoA-utilizing enzymes, offering insights into reaction mechanisms or metabolic regulation. Its synthesis and application are relevant in probing CoA-dependent processes in vitro.
Coenzyme A, S-(hydrogen 2-methylpropanedioate) structure
1264-45-5 structure
Product Name:Coenzyme A, S-(hydrogen 2-methylpropanedioate)
CAS No:1264-45-5
MF:C25H40N7O19P3S
MW:867.606887817383
CID:165059
PubChem ID:123909
Update Time:2025-06-03

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Chemical and Physical Properties

Names and Identifiers

    • Coenzyme A, S-(hydrogenmethylpropanedioate)
    • 3-[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]ethy
    • methylmalonyl-coenzyme A
    • (9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8,20-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphahenicosan-21-oic acid 3,5-dioxide (non-preferred name)
    • Coenzyme A, methylmalonyl-
    • Methylmalonyl coa
    • Methylthiomalonic acid S-ester with coenzyme A
    • Methylmalonyl-CoA
    • Methylmalonyl coenzyme A
    • Isosuccinyl coenzyme A
    • (2RS)-Methylmalonyl CoA
    • Coenzyme A, S-(hydrogen methylpropanedioate) (9CI)
    • Coenzyme A, S-(hydrogen methylmalonate) (8CI)
    • Coenzyme A, S-(hydrogen 2-methylpropanedioate)
    • ta-D-ribofuranosyl]-
    • 1264-45-5
    • Methylmalonyl coenzyme A
    • 9H-purin-6-amine,9-[5-O-[[[[[(3R)-4-[[3-[[2-[(2-carboxy-1-oxopropyl)thio]ethyl]amino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl]oxy]hydroxyphosphinyl]oxy]hydroxyphosphinyl]-3-O-phosphono-be
    • (3S,5R,9R,19E)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9,19-tetrahydroxy-8,8,20-trimethyl-10,14-dioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphahenicos-19-en-21-oic acid 3,5-dioxide (non-preferred name)
    • CHEBI:16625
    • C02557
    • 3-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-methyl-3-oxopropanoic acid
    • MZFOKIKEPGUZEN-FBMOWMAESA-N
    • SCHEMBL25429
    • METHYL-MALONYL-COA
    • Coenzyme A, S-(hydrogen methylmalonate)
    • 2-methyl-3-oxopropanoyl-CoAs
    • Methylthiomalonic acid S-ester with coenzyme A
    • methylmalonyl-CoA
    • 3'-phosphoadenosine 5'-[3-(3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methyl-3-oxopropanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl) dihydrogen diphosphate]
    • 2-Methylmalonyl-CoA
    • (2RS)-Methylmalonyl CoA
    • V0V
    • Coenzyme A, S-(hydrogen methylpropanedioate)
    • Q417791
    • GTPL5223
    • Methylmalonyl coemzyme A
    • 3-[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]ethylsulfanyl]-2-methyl-3-oxopropanoic acid
    • D0H8IT
    • Isosuccinyl coenzyme A
    • Coenzyme A, S-(hydrogen methylpropanedioate) (9CI)
    • NS00015149
    • 3-((2-(3-((2R)-4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl)thio)-2-methyl-3-oxopropanoic acid
    • CH3-malonyl-Coenzyme A
    • (S)-2-Methyl-3-oxopropanoyl-CoA
    • D-methylmalonyl-Coenzyme A
    • (S)-methyl-malonyl-CoA
    • 3-(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)ethylsulfanyl)-2-methyl-3-oxopropanoic acid
    • methyl-malonyl-coenzyme A
    • (2S)-3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid
    • L-methylmalonyl-Coenzyme A
    • (R)-methylmalonyl-Coenzyme A
    • 3-((2-(3-((2R)-3-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)methyl)-2-hydroxy-3-methylbutanamido)propanamido)ethyl)sulfanyl)-2-methyl-3-oxopropanoic acid
    • (S)-methyl-malonyl-Coenzyme A
    • 3'-phosphoadenosine 5'-(3-(3-hydroxy-2,2-dimethyl-4-((3-((2-((2-methyl-3-oxopropanoyl)sulfanyl)ethyl)amino)-3-oxopropyl)amino)-4-oxobutyl) dihydrogen diphosphate)
    • (2S)-3-((2-(3-(3-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)methyl)-2-hydroxy-3-methylbutanamido)propanamido)ethyl)sulfanyl)-2-methyl-3-oxopropanoic acid
    • Inchi： 1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12?,13-,16-,17-,18+,22-/m1/s1
    • InChI Key： MZFOKIKEPGUZEN-FBMOWMAESA-N
    • SMILES： S(C(C(C(=O)O)C)=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: 867.13125424g/mol
  • Monoisotopic Mass: 867.13125424g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 10
  • Hydrogen Bond Acceptor Count: 24
  • Heavy Atom Count: 55
  • Rotatable Bond Count: 22
  • Complexity: 1530
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -5.4
  • Topological Polar Surface Area: 426?2

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI YUAN YE Biotechnology Co., Ltd.
B71442-1mg
methylmalonyl-coenzyme A
 1264-45-5 ,
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 ￥1800.00 2024-02-20

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Production Method

Production Method 1

Reaction Conditions
1.1R:MgCl2, R:R:NaH2PO4, 3 h, 25°C, pH 7
1.2R:MeOH, cooled
Reference
Evaluating nonpolar surface area and liquid chromatography/mass spectrometry response: an application for site occupancy measurements for enzyme intermediates in polyketide biosynthesis
By Randall, Shan M. et al, Rapid Communications in Mass Spectrometry, 2014, 28(23), 2511-2522

Production Method 2

Reaction Conditions
1.1R:MgCl2, R:C:9033-20-9, S:H2O, overnight, 25°C, pH 7
1.2R:MeOH, cooled
Reference
Promiscuity of a modular polyketide synthase towards natural and non-natural extender units
By Koryakina, Irina et al, Organic & Biomolecular Chemistry, 2013, 11(27), 4449-4458

Production Method 3

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 4

Reaction Conditions
1.1S:PhMe, 4 h, 140°C
2.1R:NaHCO3, S:H2O, 10 min, 0°C
2.2R:NaHCO3, S:H2O, S:Me2CO, 0°C, pH 8.0; 12 h, 0°C
2.3R:HCl, S:H2O, pH 6.0
Reference
Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis
By Gao, Bo-Wen et al, Bioorganic & Medicinal Chemistry Letters, 2015, 25(6), 1279-1283

Production Method 5

Reaction Conditions
1.1R:MgCl2, C:9033-20-9, S:Glycerol, S:H2O, overnight, 22°C, pH 7.5
Reference
Enzymatic Extender Unit Generation for In Vitro Polyketide Synthase Reactions: Structural and Functional Showcasing of Streptomyces coelicolor MatB
By Hughes, Amanda J. and Keatinge-Clay, Adrian, Chemistry & Biology (Cambridge, 2011, 18(2), 165-176

Production Method 6

Reaction Conditions
1.1R:NaH, S:Benzene, S:(Me2N)3P=O
1.2R:KOH, S:H2O, S:EtOH
2.1R:PhSH, R:DCC, S:DMF
2.2R:NaHCO3
Reference
A rapid method for the synthesis of methylmalonyl-coenzyme A and other CoA-esters
By Padmakumar, Rugmini et al, Analytical Biochemistry, 1993, 214(1), 318-20

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Raw materials

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Preparation Products

Coenzyme A, S-(hydrogen 2-methylpropanedioate) Related Literature

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Additional information on Coenzyme A, S-(hydrogen 2-methylpropanedioate)

Comprehensive Analysis of Coenzyme A, S-(hydrogen 2-methylpropanedioate) (CAS No. 1264-45-5): Structure, Function, and Applications

Coenzyme A, S-(hydrogen 2-methylpropanedioate) (CAS No. 1264-45-5) is a specialized derivative of coenzyme A (CoA), a pivotal molecule in cellular metabolism. This compound, often abbreviated as CoA-S-MM, plays a critical role in biochemical pathways, particularly in the modification of metabolic intermediates. Its unique structure, featuring a 2-methylpropanedioate moiety linked to CoA via a thioester bond, enables it to participate in acyl transfer reactions, making it indispensable in both energy production and biosynthetic processes.

In recent years, the scientific community has shown growing interest in CoA derivatives due to their potential applications in metabolic engineering and drug development. Searches for terms like "CoA-S-MM function" and "CAS 1264-45-5 applications" have surged, reflecting its relevance in cutting-edge research. This compound is particularly notable for its role in mitochondrial metabolism, a hotspot topic linked to aging and neurodegenerative diseases. Researchers are exploring how CoA-S-MM influences acetyl-CoA levels, a key regulator of cellular energy homeostasis.

The structural integrity of Coenzyme A, S-(hydrogen 2-methylpropanedioate) is crucial for its function. The thioester linkage provides high-energy potential, facilitating the transfer of the 2-methylpropanedioate group to acceptor molecules. This mechanism is vital in fatty acid synthesis and citric acid cycle modulation. Recent studies have also highlighted its involvement in post-translational modifications, such as protein acetylation, which impacts gene expression and cellular signaling.

From an industrial perspective, CAS No. 1264-45-5 is gaining traction in biotechnology and pharmaceutical synthesis. Its ability to act as a cofactor in enzymatic reactions makes it valuable for producing high-value compounds, including antibiotics and biopolymers. Online queries like "CoA-S-MM in biomanufacturing" underscore its commercial potential. Additionally, its compatibility with green chemistry principles aligns with the global push for sustainable production methods.

Despite its niche status, CoA-S-MM exemplifies the intersection of basic research and applied science. FAQs such as "How does CoA-S-MM differ from acetyl-CoA?" or "Is CAS 1264-45-5 used in supplements?" reveal public curiosity about its practical implications. While not yet a household name, its role in metabolic health and disease therapeutics positions it as a compound to watch in the coming decade.

In summary, Coenzyme A, S-(hydrogen 2-methylpropanedioate) (CAS No. 1264-45-5) bridges fundamental biochemistry and innovative applications. Its multifaceted roles—from energy metabolism to biopharmaceuticals—make it a compelling subject for researchers and industries alike. As scientific advancements continue to unravel its potential, this compound is poised to contribute significantly to personalized medicine and industrial biotechnology.

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