Methylphosphonate Derivatives Research Articles

ChemInform Abstract: A New DMAP‐Catalyzed Phosphonamidite Coupling Reaction for Synthesis of Oligonucleotide Methylphosphonate Derivatives.

Abstract 4-N,N-dimethylaminopyridine (DMAP) catalyzed coupling of 5′-dimethoxy-tritylthymidyl-3′-methylphosphonoamidite and 5′-trifluoroacetyl-3′-acetylthymidine and subsequent oxidation produce dinucleoside methyl phosphonate in a new, less water sensitive coupling reaction.

Comparative Study of Nucleophilic am) Enzymic Reactions of 2-Propyl Methylphosphonate Derivatives

Abstract Solvent isotope effects have been measured for the reactions of 4-nitrophenyl 2-propyl methylphosphonate (IMN) with acetylcholinesterase (AChE), chymotrypsin, imidazole base, hydroxide ion, phosphate dianion, and water, and for the reactions of 2-propyl methyl phosphonofluoridate (sarin) with AChE. Kinetics and structural features of the dealkylation of AChE and chymotrypsin adducts were also studied.

Comparative Study of Nucleophilic and Enzymic Reactions of 2-Propyl Methylphosphonate Derivatives

Comparative Study of Nucleophilic and Enzymic Reactions of 2-Propyl Methylphosphonate Derivatives

A new DMAP-catalyzed phosphonamidite coupling reaction for synthesis of oligonucleotide methylphosphonate derivatives

4-N,N-dimethylaminopyridine (DMAP) catalyzed coupling of 5′-dimethoxy-tritylthymidyl-3′-methylphosphonoamidite and 5′-trifluoroacetyl-3′-acetylthymidine and subsequent oxidation produce dinucleoside methyl phosphonate in a new, less water sensitive coupling reaction.

Chemical studies of the stereochemistry of 2-substituted-1,3,2-dioxaphosphorinan-2-ones

The configurations at phosphorus in gluco-pyranoside 4,6-(R)- and (S)-methylphosphonate derivatives are established chemically by their conversion, by sequential addition of PhMgBr and EtMgBr, into (S)- and (R)-ethylmethylphenylphosphine oxides respectively; for the formation of 1,3,2-dioxaphosphorinans by phosphorus dihalide–diol reactions the kinetic preference for the thermodynamically less stable isomers depends on steric interactions in twist ring transition intermediates and the subsequent equilibration depends on the relative stabilities of the chair conformers.