10144-33-9

Upstream product

• 2177-63-1 (S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 830-03-5 4-nitrophenol acetate 
• 108-24-7 acetic anhydride 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 

Downstream Products

• 61650-30-4 N^α-Acetyl-β-benzylasparaginsaeure N-methylamid 
• 208645-73-2 Ac-Asp(OBn)-(ε-DL-hydroxy)AP(OCH3)-OCH3 
• 331843-13-1 N-acetyl-L-aspartyl-L-valinyl-L-alanine β-benzyl ester 
• 821800-06-0 3(S)-acetylamino-N-{1-[((3S)-2-benzyloxy-5-oxo-tetrahydrofuran-3-ylcarbamoyl)methyl]-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl}succinamic acid benzyl ester 
• 294871-70-8 Ac-Asp(OBn)-(ε-keto)AP(OCH3)-OCH3 
• 936846-80-9 C₄₅H₅₄N₆O₁₁ 
• 936846-81-0 C₄₅H₅₄N₆O₁₁ 
• 104870-34-0 Ac-Asp(Bzl)-Glu(Bzl)2 
• 3106-85-2 N-acetyl-L-aspartyl-L-glutamate 
• 10144-34-0 β-Benzyl-N-acetyl-L-aspartyl-O-acetyl-L-serin-methylester 

Relevant academic research and scientific papers

The Enantioselective Dakin-West Reaction

Here we report the development of the first enantioselective Dakin-West reaction, yielding α-acetamido methylketones with up to 58 % ee with good yields. Two of the obtained products were recrystallized once to achieve up to 84 % ee. The employed methylimidazole-containing oligopeptides catalyze both the acetylation of the azlactone intermediate and the terminal enantioselective decarboxylative protonation. We propose a dispersion-controlled reaction path that determines the asymmetric reprotonation of the intermediate enolate after the decarboxylation.

Synthesis and in vitro enzyme activity of peptide derivatives of bacterial cell wall biosynthesis inhibitors

The enzyme diaminopimelate aminotransferase (DAP-AT) is a good potential target for the design of novel antibacterial agents. We have synthesised a series of peptide hydrazines based on the structure of the natural substrate of DAP-AT. These compounds show varied inhibition properties in vitro vs. DAP-AT from E. coli as well as moderate antimicrobial activity vs. E. coli. Examination of the kinetics of inhibition reveals that hydrazine, as well as the substituted hydrazino-peptides, shows two-phase slow-binding inhibition. Possible mechanisms for inhibition are discussed. The Royal Society of Chemistry 2000.

N-acetylaspartylglutamic acid and its β-isomer

The α-isomer is predominantly formed in the synthesis of N-acetylaspartylglutamic acid and its β-isomer upon cleavage of N-acetylaspartic acid anhydride by the diethyl ester of glutamic acid.