3343-28-0

Usage

InChI:InChI=1/C13H9NO5/c15-10-6-5-9(13(18)19-10)14-11(16)7-3-1-2-4-8(7)12(14)17/h1-4,9H,5-6H2/t9-/m1/s1

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 3227-01-8 N-(2-Carboxy-benzoyl)-L-glutaminsaeure 
• 6349-98-0 N-phthalylglutamic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 52604-94-1 N-(2,6-dioxo-1-phenyl-piperidin-3-yl)-phthalimide 
• 102952-10-3 S-benzyl-N-(N,N-phthaloyl-γ-glutamyl)-penicillamine 
• 117876-52-5 N-[S-benzyl-N-(N,N-phthaloyl-γ-glutamyl)-penicillaminyl]-glycin-ethyl ester 
• 84139-30-0 N⁵-(4-carboxy-phenyl)-N²,N²-phthaloyl-glutamine 
• 124751-43-5 N⁵-(2-hydroxy-ethyl)-DL-glutamine 
• 82207-54-3 N,N-phthaloyl-5-thio-DL-glutamic acid S-phenyl ester 
• 52604-91-8 N⁵-phenyl-N²,N²-phthaloyl-glutamine 
• 50-35-1 thalidomide 
• 51806-96-3 α-(N-γ-DL-Glutamyl)-amino-propionitril 
• 102003-30-5 N⁵-methyl-N⁵-phenyl-N²,N²-phthaloyl-glutamine 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 94547-37-2 N⁵-benzyl-N²,N²-phthaloyl-glutamine 
• 88784-33-2 N,N-phthaloyl-DL-glutamic acid-5-benzyl ester 
• 101895-70-9 N,N-phthaloyl-glutamic acid-5-phenyl ester 

Relevant academic research and scientific papers

A novel strategy for efficient chemoenzymatic synthesis of D-glutamine using recombinant Escherichia coli cells

D-glutamine is a D type stereoisomer of glutamine which is involved in many metabolic processes. Seeking lower-cost and industrially scalable approaches for the synthesis of D-glutamine is very valuable both in academic career and potential applications. Herein, we developed a novel efficient chemoenzymatic strategy for producing D-glutamine. Initially, DL-glutamine was chemically prepared with cheap and accessible DL-glutamic acid as raw material. Subsequently, the L-glutamine among the racemic mixture was selectively hydrolyzed to L-glutamic acid by Escherichia coli whole-cell system which expressed L-aminopeptidase D-Ala-esterase/amidase (DmpA) from Ochrobactrum anthropi. The left D-glutamine was obtained by isoelectric point precipitation with 70% of the theoretical yield. Furthermore, we optimized enzymatic resolution conditions to determine the optimum parameters as pH 8, 30 °C, 0.1% (v/v) Triton X-100, and 1 mM Mn2+. These results suggested that our strategy might be potentially usable for the synthesis of D-glutamine in industrial productions.

Sulfur ylides 13. Synthesis and intramolecular cyclization of keto-stabilized sulfur ylides

Keto-stabilized sulfur mono-and bisylides were obtained from N-phthalylglutamic acid and their intramolecular cyclization was studied. The intramolecular cyclization of the ylide obtained at the α-carboxy group gave a product of the pyrrolizidinedione structure; bisylide yielded a cycloheptene derivative as the result of intramolecular recombination of intermediate dicarbene. The ylide obtained at the γ-carboxy group underwent no cyclization, giving methylthio ketone and oxo benzoate.

Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNFα-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine

Versatile synthesis of the teratogenic, TNFα-modulatory, and antiangiogenic thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine (1) and its direct antiangiogenic properties are described. With thalidomide or thalidomide derivatives as precursors, the synthesis involved either carbonyl reduction/thiation-desulfurization or carbonyl reduction/acyliminium ion reduction protocols. Compared to earlier studies with thalidomide, which was only active with microsomal treatment, 1 exhibited marginal inhibitory activity in the rat aortic ring assay, thereby demonstrating the requirement for metabolic activation.

Synthesis of 3-methylaspartic acids by ring-contraction of a nickelacycle derived from glutamic anhydride

The synthesis of protected methylaspartic acids from glutamic acid has been achieved by means of ring contraction of the derived nickelacycle followed by insertion of isocyanides.