59724-75-3

Upstream product

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

Downstream Products

• 84000-07-7 N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine 
• 1151424-90-6 N-nosyl-L-alanine benzhydryl ester 
• 1448453-31-3 C₁₀H₁₃N₃O₅S 
• 1448453-38-0 C₂₆H₄₀N₆O₁₁S₂Si₂ 
• 497820-77-6 N-nosyl-L-alanine phenacyl ester 

Relevant academic research and scientific papers

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.

Unusual reactivity of dimethylsulfoxonium methylide with esters

The dimethylsulfoxonium methylide was treated with esters under mild conditions to rapidly afford the corresponding carboxylic acids at room temperature. Moreover, by performing the procedure on enantiopure substrates, it was demonstrated that the reaction occurs without racemization. 18O-labeled reagents showed that the reaction does not proceed through an ester hydrolysis mechanism. The reactions are characterized by an unusual reactivity of the dimethylsulfoxonium methylide. This methodology is general and can be considered a valid alternate route for ester cleavage when a substrate is sensitive to hydrolysis conditions.

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-methyl-N-nosyl-β3-amino acids

(Chemical Equation Presented) N-Methyl-β3-amino acids are important building blocks in the synthesis of biologically active molecules. A very simple and efficient approach to transform natural α-amino acids into their corresponding N-methyl-βs

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

HIV protease inhibitors based on amino acid derivatives

A compound selected from the group consisting of a compound of formula I 1a compound of formula II 2and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.