3085-92-5

Usage

Uses

Used in Organic Synthesis:
N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is used as a reagent for its ability to participate in acylation and amidation reactions, which are crucial for the synthesis of various organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE serves as a precursor, contributing to the development of new drugs by providing a foundational structure that can be modified for specific therapeutic purposes.
Used in Agrochemical Production:
Similarly, in agrochemicals, N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is utilized as a starting material to create compounds that can be used in the development of pesticides, herbicides, and other agricultural chemicals.
Used in Drug Delivery Systems Development:
N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is employed in the design and synthesis of drug delivery systems, enhancing the efficiency and targeting of therapeutic agents.
Used in Peptide and Protein Conjugation for Biomedical Applications:
In the biomedical field, N-PHTHALOYL-DL-GLUTAMIC ANHYDRIDE is used for the preparation of peptide and protein conjugates, which can be instrumental in the creation of diagnostic tools, therapeutic agents, and other bioactive molecules.

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

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 3227-01-8 N-(2-Carboxy-benzoyl)-L-glutaminsaeure 
• 108-24-7 acetic anhydride 
• 6349-98-0 N-phthalylglutamic acid 
• 6893-26-1 D-Glutamic acid 
• 22911-88-2 (R)-2-phthalimidoglutaric acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 340-90-9 N-phthaloyl-L-glutamic acid 
• 112655-44-4 diethyl N,N-phtaloyl-L-glutamic acid 
• 109066-23-1 diethyl N-(2-carboxybenzoyl)-L-glutamate 
• 16450-41-2 L-glutamic acid diethyl ester 

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 
• 51806-96-3 α-(N-γ-DL-Glutamyl)-amino-propionitril 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 88784-33-2 N,N-phthaloyl-DL-glutamic acid-5-benzyl ester 
• 101895-70-9 N,N-phthaloyl-glutamic acid-5-phenyl ester 
• 111499-77-5 N,N-phthaloyl-glutamic acid-5-(4-carboxy-phenyl ester) 
• 7607-72-9 2-phthalimidoglutaramic acid 
• 42472-93-5 2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 600721-43-5 2-(1-benzyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Investigations of the Alignment Process of PBPMLG: 2H NMR Analysis Reveals a Thermoresponsive 90° Flip of the Polymer

The application of anisotropic parameters in NMR-spectroscopy enables the acquisition of spatial and angular information, complementary to those from conventional isotropic NMR-measurements. The use of alignment media is a well-established method for inducing anisotropy. PBPMLG is a recently discovered polyglutamate-based alignment medium, exhibiting thermoresponsive behavior in the lyotropic liquid crystalline (LLC) phase, thus offering potential for deeper understanding of the alignment process. We present one approach for investigating the thermoresponsive behavior by synthesizing specifically deuterated PBPMLG-isotopologues and their subsequent analyses using 2H NMR-spectroscopy. It was possible to relate the observed thermoresponsive behavior to a flip of the polymer with respect to the external magnetic field—an effect never observed before in glutamate-based polymeric alignment media. Furthermore, a solvent-induced temperature dependent gelation was verified in THF, which might provide yet another opportunity to manipulate the properties of this alignment medium in the future.

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.

Synthesis method of phthalic acylamino-L-glutamic anhydride

The invention discloses a synthesis method of phthalic acylamino-L-glutamic anhydride. The method comprises the following steps: firstly, ensuring that phthalic anhydride and L-glumatic acid react for4 to 8 hours at 80 to 85 DEG C with the existence of an acid-binding agent, and adjusting pH with hydrochloric acid till N-phthaloyl-L-glutamic acid is separated out; secondly, adding acetic anhydride to the N-phthaloyl-L-glutamic acid obtained in the first step, performing reflux reaction, naturally cooling to room temperature, ensuring that white solid is separated out, separating, and drying,so as to obtain the phthalic acylamino-L-glutamic anhydride. The synthesis method is short in route, easy to operate, high in yield, low in pollution, and more environmentally friendly, ensures that the production cost is greatly reduced, and has a good application prospect.

Poly-γ-p-Biphenylmethyl-Glutamate as Enantiodifferentiating Alignment Medium for NMR Spectroscopy with Temperature-Tunable Properties

The use of anisotropic NMR parameters—especially residual dipolar couplings (RDCs)—offers access to additional structural information and, therefore, alignment media required for this approach are under a continuous development. Here, we present poly-γ-p-biphenylmethyl-glutamate (PBPMG) as a new versatile enantiodifferentiating alignment medium. The thermoresponsive properties of this polymer allowed for RDC measurements of more than one orientation within the same sample at different temperatures. Moreover, the outstanding enantiodifferentiation along with excellent spectral quality even offered the opportunity to differentiate enantiomers in mixtures.

Synthesis of amphiphilic alternating polyesters with oligo(ethylene glycol) side chains and potential use for sustained release drug delivery

Novel amphiphilic alternating polyesters, poly((N-phthaloyl-l-glutamic anhydride)-co-(2-(2-(2-methoxyethoxy)ethoxy)methyl)oxirane) (P(PGA-co-ME 2MO)), were synthesized by alternating copolymerization of PGA and ME2MO. The structures of the synthesized polyesters were characterized by 1H NMR, 13C NMR, FT-IR, and GPC analyses. Because of the presence of oligo(ethylene glycol) (OEG) side chains, the polyesters could self-assemble into thermosensitive micelles. Dynamic light scattering (DLS) showed that these micelles underwent thermoinduced size decrease without intermicellar aggregation. In vitro methyl thiazolyl tetrazolium (MTT) assay demonstrated that the polyesters were biocompatible to Henrietta Lacks (HeLa) cells, rendering their potential for drug delivery applications. Two hydrophobic drugs, rifampin and doxorubicin (DOX), were loaded into the polyester micelles and observed to be released in a zero-order sustained manner. The sustained release could be accelerated in lower pH or in the presence of proteinase K, due to the degradation of the polyester under these conditions. Remarkably, in vitro cell experiments showed that the polyester micelles accomplished fast release of DOX inside cells and higher anticancer efficacy as compared with the free DOX. With enhanced stability during circulation condition and accelerated drug release at the target sites (e.g., low pH or enzyme presence), these novel polyesters with amphiphilic structures are promising to be used in sustained release drug delivery systems.

Novel Dipeptides incorporating selenoamino acids with enhanced bioavailability- Synthesis, pharmaceutical and cosmeceutical applications thereof

Disclosed is a novel synthetic method for isomeric peptides through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid. The novel synthetic method produces isomeric peptides of L-selenomethionine or Se-Methyl-L-selenocysteine that exhibit (i) enhanced water solubility; (ii) enhanced rate of dissolution in water; (iii) enhanced bioavailability; (iv) excellent vascular endothelial growth factor promoting activity; (v) excellent anti-5-alpha-reductase activity; (vi) capabilities to prevent/reduce “hair fall” and promote “hair growth”, thereby maintaining a perfect homeostasis for “hair care”. Cosmeceutical and pharmaceutical compositions comprising the isomeric peptides obtained through an appropriate linkage of L-selenomethionine or Se-Methyl-L-selenocysteine with L-glutamic acid are also disclosed. Other dipeptides with several other amino acids and uses thereof are also disclosed.

γ-Glutamyl dipeptides in Petiveria alliacea

Three γ-glutamyl dipeptides have been isolated from Petiveria alliacea L. roots. These dipeptides include (SC2RC7)- γ-glutamyl-S-benzylcysteine together with two diastereomeric sulfoxides, namely (SC2RC7RS)- and (SC2R C7RS)-γ-glutamyl-S-benzylcysteine S-oxides (γ-glutamyl-petiveriins A and B, respectively). Their structures and absolute configurations have been determined by NMR, MALDI-HRMS, IR and CD spectroscopy, and confirmed by comparison with authentic compounds obtained by synthesis.

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.