18916-93-3Relevant academic research and scientific papers
Synthesis of δ-L-α-aminoadipoyl-L-cysteinyl- D-allylglycine, and eight deuterated analogues, substrates for the investigation of the mechanism of action of isopenicillin n synthase
Baldwin, Jack E.,Bradley, Mark,Turner, Nicholas J.,Adlington, Robert M.,Pitt, Andrew R.,Sheridan, Helen
, p. 8203 - 8222 (2007/10/02)
The synthesis of δ-L-α-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allyglycine residue.
The Configurational Stability of Vinyl Carbanions Derived from Monosubstituted Activated Ethylenes
Feit, Ben-Ami,Melamed, Uri,Speer, Heike,Schmidt, Richard R.
, p. 775 - 780 (2007/10/02)
The configurational stability of vinyl carbanions derived from the 1-substituted activated ethylenes, acrylonitrile and methyl acrylate, was investigated.The pure cis-isomers of the corresponding β-deuterioolefins were treated with benzophenone in the presence of a base in several solvents (diethyl ether, tetrahydrofuran, and diethyl ether-hexane). cis-trans Mixtures of the corresponding α-> derivatives formed were isolated and their composition determined.The mechanism of the formation of the two isomeric products is discussed.The vinyl carbanion derived from the β-deuterioacrylonitrile was configurationally stable, while that derived from the corresponding acrylic ester was configurationally unstable.
