23926-58-1

Upstream product

• 64-17-5 ethanol 
• 6968-11-2 N,N'-bis-benzyloxycarbonylcystine 
• 501-53-1 benzyl chloroformate 
• 56-89-3 L-cystine 
• 98346-43-1 N-benzyloxycarbonyl-L-cystine diethyl ester; hydrochloride 
• 22735-07-5 L-cystine diethyl ester dihydrochloride 
• 6968-11-2 N,N'-bis(benzyloxycarbonyl)-L-cystine 

Downstream Products

• 23926-59-2 (R)-2-benzyloxycarbonylamino-3-chlorosulfopropanoic acid ethyl ester 
• 98330-14-4 N¹-(benzyloxycarbonyl)-N²-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cystine ethyl tert-butyl diester 
• 98303-75-4 N¹-(benzyloxycarbonyl)-N²-(tert-butyloxycarbonyl)-L-cystine ethyl tert-butyl diester 
• 1464-43-3 seleno-L-cystine 
• 98303-77-6 C₂₆H₃₂N₂O₉S₂ 
• 95084-26-7 N-(benzyloxycarbonyl)-L-cysteine ethyl ester 
• 26527-27-5 N,N'-Di-(benzyloxycarbonyl)-meso-lanthionin-diethylester 
• 37924-61-1 2-Ethoxycarbonyl-2-benzyloxycarbonylamino-ethan-sulfochlorid 

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.