145641-43-6

Upstream product

• 145641-42-5 N-phenylalanine methyl ester 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 145641-39-0 ((S)-1-Chlorosulfinylmethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 122818-32-0 (S)-2-<(tert-Butoxycarbonyl)amino>-3-phenylpropyl thioacetate 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 67-56-1 methanol 
• 35661-40-6 N-Fmoc L-Phe 
• 184916-33-4 ((S)-1-Chlorosulfonylmethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 

Downstream Products

• 167867-49-4 (S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propane-1-sulfonylamino)-3-phenyl-propionic acid 

Relevant academic research and scientific papers

Solid-phase synthesis of peptidosulfonamide containing peptides derived from Leu-enkephalin

Using Boc or Fmoc-protected β-substituted aminoethanesulfonyl chlorides (2-substituted taurylchlorides) the solid-phase synthesis of dipeptidosulfonamides as well as peptidosulfonamide containing peptides derived from Leu-enkephalin is described. The binding activity of the peptidosulfonamide YGGFL derivatives is reported.

Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere

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.

Synthesis of peptides containing the β-substituted aminoethane sulfinamide or sulfonamide transition-state isostere derived from amino acids

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.