98330-14-4

Upstream product

• 98303-79-8 N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester 
• 98303-77-6 C₂₆H₃₂N₂O₉S₂ 
• 23926-58-1 N,N'-bis(benzyloxycarbonyl)-L-cystine diethyl ester 
• 38261-78-8 (2R,2'R)-di-tert-butyl 3,3'-disulfanediylbis(2-aminopropanoate)dihydrochloride 
• 501-53-1 benzyl chloroformate 
• 98303-74-3 N,N'-bis<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cystine di-tert-butyl ester 
• 98303-78-7 C₂₀H₃₀Cl₆N₂O₉S₂ 

Relevant academic research and scientific papers

Conversion of Thiosulfinate Derivatives of Cystine to Unsymmetrical Cystines and Lanthionines by Reaction with Tris(dialkylamino)phosphines

Synthetic routes to the unsymmetrical lanthionines 2 and 3 have been developed.Reaction of a thiosulfinate, derived by oxidation of the corresponding symmetrical cystine with m-chloroperbenzoic acid, with a protected cysteine in the presence of a tris(dialkylamino)phosphine, hexaethylphosphorus triamide, yielded an unsymmetrical or mixed cystine.Contraction of the disulfide linkage in the appropriate mixed cystine by reaction with hexaethylphosphorus triamide provided the unsymmetrical lanthionines 2 and 3.A second route to unsymmetrical lanthionines was investigated that involved the attempted displacement of sulfonate leaving groups from di- or tripeptides containing a serylvaline residue.The sulfonate ester function was observed to be very unreactive toward displacement by mercaptide anion in these peptides, a fact that may be due to steric or conformational effects originating from the adjacent valine residue.