869646-27-5

Basic information

• Product Name: L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-[[(4-methylphenyl)methyl]seleno]-
• CAS NO: 869646-27-5
• Molecular Formula: C16H23NO4Se
• Molecular Weight: 372.323
• Mol File: 869646-27-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-[[(4-methylphenyl)methyl]seleno]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-[[(4-methylphenyl)methyl]seleno]-(869646-27-5)
• EPA Substance Registry System: L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-[[(4-methylphenyl)methyl]seleno]-(869646-27-5)

Safety Data

• Hazardous Substances Data: 869646-27-5(Hazardous Substances Data)

Upstream product

• 170848-34-7 methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate 
• 69961-11-1 2-tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 
• 3850-40-6 N-Boc-DL-serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 877754-71-7 (2R,2'R)-3,3'-diselanediylbis(2-((tert-butoxycarbonyl)amino)propanoic acid) 
• 104-81-4 4-Methylbenzyl bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 56926-94-4 methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 65915-30-2 bis-4-(methylbenzyl)-diselenide 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 922178-75-4 p-tolyl-methaneselenol 

Relevant articles and documents

Improved synthetic routes to the selenocysteine derivatives useful for Boc-based peptide synthesis with benzylic protection on the selenium atom

Selenocysteine (Sec) derivatives, i.e., Boc-Sec(MBn)-OH (1) and Boc-Sec(MPM)-OH (2), which are useful for chemical synthesis of selenopeptides, were obtained from L-serine in five steps with total yields of 73% and 74%, respectively. The enantiomeric excesses were confirmed to be >99% e.e. by optical resolution using a chiral column on HPLC. On the other hand, for the case of a Fmoc-protected Sec derivative, i.e., Fmoc-Sec(MPM)-OH, similar reactions resulted in low yields and partial racemization taking place. [PRESENTED EQUATION]

Strategic use of non-native diselenide bridges to steer oxidative protein folding

Targeted insertion of a non-native diselenide cross-link into a cysteine-rich protein can be exploited to direct the early stages of oxidative folding so as to avoid accumulation of unproductive intermediates that limit folding efficiency. This simple strategy could facilitate the production of many difficult-to-fold peptides and proteins. Copyright