145641-41-4Relevant academic research and scientific papers
Synthesis of peptides containing the β-substituted aminoethane sulfinamide or sulfonamide transition-state isostere derived from amino acids
Moree, Wilna J.,Van Der Marel, Gijs A.,Liskamp Rob
, p. 6389 - 6392 (1992)
α-amino acids can be converted to homochiral β-substituted aminoethane sulfinamide or sulfonamide transition-state isosteres, which can be incorporated into peptides. These transition-state analogues e.g. the sulfonamide isostere of Phe-Phe will be used for the generation of catalytic antibodies as well as for the development of protease inhibitors.
Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere
Moree, Wilna J.,Marel, Gijs A. van der,Liskamp, Rob J.
, p. 5157 - 5169 (2007/10/02)
Synthetic routes are described toward the preparation of α- as well as β-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative.The sulfinyl chlorides are used as building blocks for the preparation of homochiral α- or β-substituted sulfinamide and sulfonamide transition-state isosteres.The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors.In addition, the β-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.
