1264-45-5

Basic information

• Product Name: methylmalonyl-coenzyme A
• Synonyms: methylmalonyl-coenzyme A
• CAS NO: 1264-45-5
• Molecular Formula: C₂₅H₄₀N₇O₁₉P₃S
• Molecular Weight: 867.606883
• Mol File: 1264-45-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.92g/cm³
• Refractive Index: 1.72
• CAS DataBase Reference: methylmalonyl-coenzyme A(CAS DataBase Reference)
• NIST Chemistry Reference: methylmalonyl-coenzyme A(1264-45-5)
• EPA Substance Registry System: methylmalonyl-coenzyme A(1264-45-5)

Safety Data

• Hazardous Substances Data: 1264-45-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of malonyl-CoAs that is malonyl-CoA carrying a methyl group on the malony side chain.

InChI:InChI=1/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

Upstream product

• 85-61-0 coenzyme A 
• 317-66-8 S-propionyl-coenzyme-A 
• 516-05-2 methyl-propanedioic acid 
• 900498-43-3 coenzyme A 

Downstream Products

• 604-98-8 succinyl-coenzyme A 
• 524735-63-5 4-hydroxy-3,5-dimethyl-6-pentyl-pyran-2-one 

Related news

A Rapid Method for the Synthesis of methylmalonyl-coenzyme A (cas 1264-45-5) and Other CoA-Esters08/14/2019

A rapid and high-yield synthesis of methylmalonyl coenzyme A is reported. The two-step procedure involves preparation of the thiophenyl ester of methylmalonic acid using dicyclohexylcarbodiimide as a condensing agent, followed by transesterification with coenzyme A, to yield methylmalonyl coenzy...detailed

Comparison of two methods for the measurement of rat liver methylmalonyl-coenzyme A (cas 1264-45-5) mutase activity: HPLC and radioisotopic assays08/13/2019

Methylmalonyl-coenzyme A mutase (MCM) is a 5′-deoxyadenosylcobalamin-linked mitochondrial enzyme that catalyzes the isomerization of L-methylmalonyl-coenzyme A to succinyl-coenzyme A. In vitro assays of total and holo-MCM activities are important tools for investigating the cobalamin pathway. S...detailed

How coenzyme B12 radicals are generated: the crystal structure of methylmalonyl-coenzyme A (cas 1264-45-5) mutase at 2 å resolution08/12/2019

Background: The enzyme methylmalonyl-coenzyme A (CoA) mutase, an αβ heterodimer of 150 kDa, is a member of a class of enzymes that uses coenzyme B12 (adenosylcobalamin) as a cofactor. The enzyme induces the formation of an adenosyl radical from the cofactor. This radical then initiates a free-...detailed

Influence of carbon and nitrogen source on synthesis of NADP+-isocitrate dehydrogenase, methylmalonyl-coenzyme A (cas 1264-45-5) mutase, and methylmalonyl-coenzyme A (cas 1264-45-5) decarboxylase in Saccharopolyspora erythraea CA34008/10/2019

Methylmalonyl-coenzyme A (CoA) mutase, methylmalonyl-CoA decarboxylase and NADP+-isocitrate dehydrogenase activity profiles were determined in Saccharopolyspora erythraea CA340, an erythromycin producer, grown in glucose or ammonium chloride. Results show that methylmalonyl-CoA mutase and isocit...detailed

Relevant articles and documents

Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis

(Methyl)malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl)malonate from (methyl)Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl)malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone.

Establishing a toolkit for precursor-directed polyketide biosynthesis: Exploring substrate promiscuities of acid-CoA ligases

Polyketides are chemically diverse and medicinally important biochemicals that are biosynthesized from acyl-CoA precursors by polyketide synthases. One of the limitations to combinatorial biosynthesis of polyketides has been the lack of a toolkit that describes the means of delivering novel acyl-CoA precursors necessary for polyketide biosynthesis. Using five acid-CoA ligases obtained from various plants and microorganisms, we biosynthesized an initial library of 79 acyl-CoA thioesters by screening each of the acid-CoA ligases against a library of 123 carboxylic acids. The library of acyl-CoA thioesters includes derivatives of cinnamyl-CoA, 3-phenylpropanoyl-CoA, benzoyl-CoA, phenylacetyl-CoA, malonyl-CoA, saturated and unsaturated aliphatic CoA thioesters, and bicyclic aromatic CoA thioesters. In our search for the biosynthetic routes of novel acyl-CoA precursors, we discovered two previously unreported malonyl-CoA derivatives (3-thiophenemalonyl-CoA and phenylmalonyl-CoA) that cannot be produced by canonical malonyl-CoA synthetases. This report highlights the utility and importance of determining substrate promiscuities beyond conventional substrate pools and describes novel enzymatic routes for the establishment of precursor-directed combinatorial polyketide biosynthesis. (Chemical Presented).