Methoxycarbonyl phosphate

Methoxycarbonyl phosphate/acetate kinase. Methoxycarbonyl phosphate (MCP 3) was designed to replace AcP as phosphoryl donor1181. It is comparable to PEP in its high phosphorylating strength (see Table 13-2), but resembles acetyl phosphate in its ease of synthesis. Aqueous solutions of MCP are prepared from aqueous phosphate and methyl chloroformate and used in ATP regeneration without purification. The reaction product after phosphoryl transfer is methyl carbonate, which hydrolyses rapidly to form C02 and MeOH. Product isolation is simple and bicarbonate inhibition can be avoided by purging the reaction mixture. 

MCP is accepted as an unnatural substrate by AcK (E.C. 2.7.2.1) and CK (E. C. 2.7.2.2) but not by PK,1k. The principal disadvantage of methoxycarbonyl phosphate as phosphorylating agent in ATP regeneration is MCP s rapid spontaneous decomposition. The half-life of MCP in aqueous solution is only 0.3 h (25 °C, pH 7) 18). Because of this short half-life, MCP is only used in a few cases where high phosphorylating potentials are required to push the phosphorylation reaction to the product side (see Table 13-4, entry 20). 

AcK acetate kinase AcP acetyl phosphate AdK adenylate kinase AP A p ,pn-di(adenosine 5 -) n-phosphate ARS aminoacyl tRNA synthetase ATP, ADP, AMP adenosine 5 -tri-, di-, monophosphate ATP-u-S (Sp)-adenosine 5 -0-(l-thiotriphos-phate), ATP-y-S adenosine 5 -0-(3-thiotriphosphate) CK carbamyl kinase CP carbamyl phosphate CrK creatine kinase CTP, CDP, CMP cytidine 5 -tri-, di-, monophosphate dATP, dAMP deoxyadenosine 5 -tri-, monophosphate DNA deoxyribonucleic acid AG change in free energy GK glycerol kinase GTP, GDP, GMP guanosine 5 -tri-, di-, monophosphate HK hexokinase IUB International Union of Biochemistry MCP methoxycarbonyl phosphate NTP, NDP, NMP nucleoside 5 -tri-, di-, monophosphate PC phosphocreatine PEP phosphoenol pyruvate P orthophosphate PK pyruvate kinase P polyphosphate PnK poly-... 

Methoxyaniline, see o-Anisidine p-Methoxyaniline, see p-Anisidine 2-Methoxybenzenamine, see o-Anisidine 4-Methoxybenzenamine, see p-Anisidine p-Methoxybenzenamine, see p-Anisidine Methoxycarbonylethene, see Methyl acrylate Methoxycarbonylethylene, see Methyl acrylate 2-Methoxycarbonyl-l-methylvinyl dimethyl phosphate, see... 

Mevinphos [7786-34-7], 0,0-dimetliyl 0-(2-methoxycarbonyl-l-methylvmyl) phosphate, (CH30)2P(0)C(CH3)=CHC(0)0CH3 (bp 106—107°C at 0.13 kPa, d 1.25, vp 0.38 Pa at 21°C), is a mixture of one part cis and two parts trans isomers, of which the cis isomer is about 10-fold more effective. It is miscible with water and rat LD5Qs are 6.1, 3.7 (oral) and 4.7,4.2 (dermal) mg/kg. Mevinphos is a nonpersistent systemic insecticide suitable for the treatment of edible produce dose to harvest, because of rapid dissipation of the residue by hydrolysis and volatilization. 

Chemical Name 2-carbomethoxy-l-methylvinyl dimethyl phosphate l-methoxycarbonyl-l-propen-2-yl dimethyl phosphate methyl-3-(dimethoxyphosphinoyloxy)but-2-enoate 2-carbomethoxy-l-methylvinyl dimethyl phosphate Uses contact insecticide and acaricide to control chewing insects and spider mites in fruits, vegetables, and ornamentals. CAS Registry No 7786-34-7 [formerly 298-01-1 for (E) isomer 338-45-4 for (Z) isomer] for cis-isomer and 338-45-4 for trans-isomer]... 

IUPAC name 2-methoxycarbonyl-l-methylvinyl dimethyl phosphate Molecular formula C7H1306P Toxicity class USEPA I WHO la... 

More recently, the use of the chloroformate-aqueous alkali method has been revived by G. R. Barker and his associates in order to prepare a suitably protected D-ribose carbonate for a synthesis of a-D-ribofuranosyl phosphate. (An analogous synthesis of the latter compoimd, involving a phosgene-pyridine reaction, appeared almost simultaneously. ) Condensation of D-ribose with methyl chloroformate in the presence of aqueous sodium hydroxide led to the formation of a mixture of the anomers of l,5-di-0-(methoxycarbonyl)-D-ribofuranose 2,3-carbonate (LII), which was resolved by fractional recrystallization. The treatment of either of the derived D-ribofuranosyl chlorides with methanol and silver carbonate... 

Structure 4.7 0 ° i 1 CHjO p O C=C C OCHj 1 i OCH3 H Mevinphos Dimethyl 2-methoxycarbonyl-l-methylvinyl Phosphate... 

SYNS APAVINPHOS a-2-CARBOMETHOXY-l-xMETHYLVINYL DIMETHYL PHOSPHATE 2-CARBOMETHOXY-1-PROPEN-2-YL DIMETHYL PHOSPHATE CMDP COMPOUND 2046 3-((DIMETHOXYPHOSPHINYL)OXY)-2-BUTENOIC ACID METHYL ESTER 0,0-DIMETHYL-0-(2-CARB0-METHOXY-l-METHYLVlNYL) PHOSPHATE DIMETHYL-1 -CARBOMETHOXY-1-PROPEN-2-YL PHOSPHATE DIMETHYL ESTER PHOSPHORIC ACID ESTER with METHYL 3-HYDROXYCROTONATE 0,0-DIMETHYL-0-2-METHOXYCARBONYL-1-METHYL-VINYL-PHOSPHAT (GERMAN) DIMETHYL 2-METHOXYCARBONYL-l-METHYLVINYL PHOSPHATE... 

DIMETHYL METHOXYCARBONYLPROPENYL PHOSPHATE DIMETHYL (1-METHOXYCARBOXY-PROPEN-2-YL)PHOSPHATE 0,0-DIMETHYL 0-(l-METHYL-2-CARBOXYV1NYL) PHOSPHATE DURAPHOS ENT 22,374 FOSDRIN GESFID GESTID 3-HYDROXYCROTONIC ACID METHYL ESTER DIMETHYL PHOSPHATE MENIPHOS MENITE O (2-METHOXYCARBONYL-l-METHYL-VINYL)-DIMETHYL-FOSFAAT (DUTCH) (2-METHOXYCARBONYL-l-METHYL-VINYL)-DIMETHYL-PHOSPHAT (GERMAN) 2-METHOXYCARBONYL-l-METHYLVINYL DIMETHYLPHOSPHATE 1-METHOXYCARBONYL-1-PROPEN-2-YL DIMETHYL PHOSPHATE (l-METHOXYCARBOXYPROPEN-2-YL)PHOSPHORIC ACID, DIMETHYL ESTER METHYL-3-... 

PHOSDRIN (OSHA) PHOSFENE PHOSPHATE de DIMETHYLE et de 2-METHOXYCARBONYL-l METHYLVINYLE (FRENCH) PHOSPHENE (FRENCH)... 

O, 0-DIMETHYL-0-2-METH0XYCARB0NYL-1 -METHYL-VINYL-PHOSPHAT (GERMAN) see MQR750 DIMETHYL 2-METHOXYCARBONYL-l-METHYLVINYL PHOSPHATE see MQR750 DIMETHYL METHOXYCARBONYLPROPENYL PHOSPHATE see MQR750... 

METHOXYCARBONYL-1-PROPEN-2-YI-DIMETHYL PHOSPHATE see MQR750 (1-METH0XYCARB0XYPR0PEN-2-YL)PH0SPH0RIC ACID, DIMETHYL ESTER see MQR750 METHOXYCHLOR see MEI450 p,p -METHOXYCHLOR see MEI450... 

CROTONIC ACID, 3-HYDROXY-, MEHYL ESTER, DIMETHYL PHOSPHATE DIMEHYL(1-METHOXYCARBOXYPROPEN-2-YL)PHOSPHATE DIMETHYL 2-METHOXYCARBONYL-1-METHYLVINYL PHOSPHATE DIMETHYL METHOXYCARBONYLPROPENYL PHOSPHATE DIMETHYL-1 -CARBOMETHOXY-1-PROPEN-2-YL PHOSPHATE DURAPHOS... 

DIMETHYL O-( 1-CARBOMETHOXY-1-PROPEN-2-YL) PHOSPHATE O.O-DIMETHYL-0(2-CARB0METHYL-O-(2-CARBOMETH0XY-1 -METHYLVINYL) PHOSPHATE O,O-DIMETHYL-O-2-METHOXYCARBONYL-1 -METHYL-VINYL-PHOSPHAT (GERMAN)... 

METHOXYCARBONYL-1-METHYLVINYL DIMETHYL PHOSPHATE 2-BUTENOIC ACID. 3-((DIMETHOXYPHOSPHINYL)OXY)-,METHYL ESTER (SCI) 2-CARBOMETHOXY-1-METHYLVINYL DIMETHYL PHOSPHATE... 

Synonyms Apavinphos 2-Butenoic acid 3-((dimethoxyphosphinyl)oxy)methyl ester 2-Carbomethoxy-l-methylvinyl dimethyl phosphate a-Carbomethoxy-l-methylvinyl dimethyl phosphate 2-Carbomethoxy-l-propen-2-yl dimethyl phosphate CMDP Compound 2046 3-((Dimethoxyphosphinyl)oxy)-2-butenoic acid methyl ester 0,0-Dimethyl-0-(2-carbomethoxy-1 -methylvinyl)phosphate Dimethyl-1 -carbomethoxy-1 -propen-2-yl phosphate (9,0-Dimethyl 1-carbomethoxy-l-propen-2-yl phosphate Dimethyl 2-methox-ycarbonyl-l-methylvinyl phosphate Dimethyl methoxycarbonylpropenyl phosphate Dimethyl (l-methoxycarboxypropen-2-yl)phosphate 0,0-Dimethyl 0-(l-methyl-2-carbox-yvinyl)phosphate Dimethyl phosphate of methyl-3-hydroxy-c/5 -crotonate Duraphos ENT 22324 Fosdrin Gesfid Gestid 3-Hydroxycrotonic acid methyl ester dimethyl phosphate Meniphos Menite 2-Methoxycarbonyl-l-methylvinyl dimethyl phosphate c/5 -2-Methoxycarbonyl-l-methylvinyl dimethyl phosphate l-Methoxycarbonyl-l-propen-2-yl dimethyl phosphate Methyl 3-(dimethoxyphosphinyloxy)crotonate NA 2783 OS 2046 PD 5 Phosdrin c/.s-Phosdrin Phosfene Phosphoric acid (l-methoxycarboxypropen-2-yl) dimethyl ester. 

Dimethyl-1-hydroxy-2,2,2-trichloroethyl phosphonate, see Trichlorfon (9,(9-Dimethyl-(l-hydroxy-2,2,2-trichloro)ethyl phosphate, see Trichlorfon (9,(9-Dimethyl-(l-hydroxy-2,2,2-trichloro)ethyl phosphonate, see Trichlorfon Dimethyl 2-methoxycarbonyl-l-methylvinyl phosphate, see Mevinphos Dimethyl methoxycarbonylpropenyl phosphate, see Mevinphos Dimethyl (l-methoxycarboxypropen-2-yl)phosphate, see Mevinphos (9,(9-Dimethyl S -(5-methoxy-l,3,4-thiadiazolittyl-3-methyl) dithiophosphate, see Methidathion... 

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