59724-75-3

Basic information

• Product Name: N-(p-nitrophenylsulfonyl)-(S)-alanine
• Synonyms: N-(p-nitrophenylsulfonyl)-(S)-alanine
• CAS NO: 59724-75-3
• Molecular Weight: 274.254
• Mol File: 59724-75-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-(p-nitrophenylsulfonyl)-(S)-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-nitrophenylsulfonyl)-(S)-alanine(59724-75-3)
• EPA Substance Registry System: N-(p-nitrophenylsulfonyl)-(S)-alanine(59724-75-3)

Safety Data

• Hazardous Substances Data: 59724-75-3(Hazardous Substances Data)

Upstream product

• 329912-92-7 (2S)-methyl 2-(4-nitrobenzenesulfonamido)propanoate 
• 1356918-70-1 N-Nosyl-L-alanine ethyl ester 
• 56-41-7 L-alanin 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 244250-20-2 N-(p-nitrophenyl)sulfonyl-L-alanyl chloride 
• 399559-47-8 2-[N-(p-aminophenyl)sulfonyl-(S)-alanyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-1-(3,4-dimethoxyphenethyl)isoquinoline 
• 244250-31-5 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline 
• 1151424-90-6 N-nosyl-L-alanine benzhydryl ester 

Relevant articles and documents

The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters

The dimethylsulfoxonium methylide is described as a unique and useful reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters. The new methodology was applied successfully both to solution- and solid-phase peptide synthesis. The adopted methodology was extended successfully also to peptides containing amino acids bearing acid-sensitive protecting group in side chains. Furthermore no measurable epimerization was observed in the deprotection reaction of N-Fmoc-dipeptide methyl esters with dimethylsulfoxonium methylide.

Synthesis of constrained peptidomimetics containing 2-oxo-1,3-oxazolidine- 4-carboxylic acids

Sulfonyl peptides containing a serine or threonine residue undergo cyclization with bis(succinimidyl) carbonate (DSC) and diisopropylethylamine (DIPEA) to give peptides with a 2-oxo-1,3-oxazolidine-4-carboxylate (Oxd) group, either in solution or in the solid phase. The position of the serine or threonine residue in the sequence is relatively unimportant. Under the same conditions, the corresponding Fmoc- or Boc-peptides gave dehydration products, in agreement to previous studies. The protocol constitutes a valuable approach to the preparation of oxazolidinone-containing peptides, which are a recently emerging class of constrained peptidomimetics. As a representative example, an Oxd analogue of the endogenous opioid peptide endomorphin-1, characterized by an all-trans conformation, was readily prepared.

N-methylation of peptides on selected positions during the elongation of the peptide chain in solution phase

An efficient and general solution-phase method for the site-specific N-methylation of peptides has been developed. This novel procedure involves synthesis of N-nosyl protected peptides and their subsequent N-methylation with diazomethane. Its efficiency w