50997-19-8

Usage

InChI:InChI=1/C14H15NO5/c1-20-14(19)11(9-10-5-3-2-4-6-10)15-12(16)7-8-13(17)18/h2-8,11H,9H2,1H3,(H,15,16)(H,17,18)/b8-7-/t11-/m0/s1

Upstream product

• 108-31-6 maleic anhydride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 L-phenylalanine methyl ester 
• 2577-90-4 (D)-Phenylalaninmethylester 

Downstream Products

• 62205-63-4 methyl N,N-maleoyl-L-phenylalaninate 
• 144965-45-7 N-Benzyl-α-aspartyl-(β-benzyl)-(L)-phenylalaninmethylester 
• 144965-45-7 N-Benzyl-α-aspartyl-(β-benzyl)-(D)-phenylalaninmethylester 
• 57079-18-2 N-maleyl-L-phenylalanine 

Relevant academic research and scientific papers

Synthesis and properties of chiral N,N-maleoyl derivatives and Diels-Alder reactions with cyclopentadiene

Maleyl amino acid derivatives were prepared from maleic anhydride and cyclized by reaction with ZnCl2 and hexamethyldisilazane yielding maleoyl derivatives. These derivatives were used as dienophiles in cycloadditions with cyclopentadiene. The

Synthesis and antimicrobial activities of N-substituted imides

In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.

Synthetic and NMR-Spectroscopic Investigation of Benzylamine Addition to N-Maleylamino Acid Derivatives

During the addition of amines to maleylamino acids in general β-amino derivatives are formed.In order to change the reactivity within the vinylogous maleyl system we introduced the β-benzylester group into the starting compound N-(cis-β-carboxyacryloyl)-phenylalanine methylester 1.The obtained benzylester 2 is adding benzylamine in α-position yielding N-benzyl-α-aspartyl(β-benzyl)-phenylalanine methylester 4.The addition reaction was investigated by 1H-NMR-spectroscopy.The structures of the compounds have been confirmed by elemental analysis, IR, 1H-NMR and 13C-NMR spectroscopy.Keywords. α-Aspartyl peptides; N-Maleylamino acid derivatives; Nucleophilic addition.