2791-79-9

Usage

Uses

Used in Pharmaceutical Industry:
Dibenzyl L-aspartate is used as a protected intermediate for L-aspartic acid in the pharmaceutical industry. The protection of the carboxylic acid group by the benzyl groups allows for selective reactions at other functional groups within the molecule, facilitating the synthesis of complex pharmaceutical compounds.
Used in Biochemical Research:
In the field of biochemical research, Dibenzyl L-aspartate is utilized as a stable and protected form of L-aspartic acid. This allows researchers to study the properties and interactions of aspartic acid in various biological systems without the risk of unwanted side reactions or degradation.
Used in Drug Development:
Dibenzyl L-aspartate is used as a key building block in the development of new drugs targeting various diseases and conditions. The protected nature of the molecule enables the creation of novel drug candidates with improved pharmacological properties, such as enhanced stability, bioavailability, and target specificity.
Used in Peptide Synthesis:
In peptide synthesis, Dibenzyl L-aspartate is employed as a protected amino acid, allowing for the controlled assembly of peptide chains with specific sequences and functions. The protection of the carboxylic acid group by the benzyl groups ensures that the aspartic acid residue can be selectively incorporated into the growing peptide chain without interference from other functional groups.
Used in Chemical Synthesis:
Dibenzyl L-aspartate is also used in various chemical synthesis processes, where the protected nature of the molecule allows for the selective modification of other functional groups within the molecule. This can lead to the development of new chemical compounds with unique properties and applications in various industries, such as materials science, agriculture, and environmental science.

Upstream product

• 5241-60-1 di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 56-84-8 L-Aspartic acid 
• 100-51-6 benzyl alcohol 
• 56612-93-2 dibenzyl N-(tert-butoxycarbonyl)glycyl-L-aspartate 
• 100-39-0 benzyl bromide 
• 2886-33-1 dibenzyl L-aspartate toluene-4-sulphonate 
• 73984-07-3 N-Tosyl-L-aspartic acid α,β-dibenzyl ester 
• 13726-67-5 Boc-Asp-OH 
• 104-15-4 toluene-4-sulfonic acid 
• 80974-42-1 (S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 

Downstream Products

• 95940-33-3 N-(3-Carboxy-propionyl)-L-asparaginsaeure-dibenzylester 
• 61058-43-3 N-Carbobenzoxy-β-alanyl-L-asparaginsaeuredibenzylester 
• 56612-93-2 dibenzyl N-(tert-butoxycarbonyl)glycyl-L-aspartate 
• 72776-06-8 (L)-N-(trimethylsilyl)dibenzyl aspartate 
• 91103-43-4 (S)-2-{(R)-2-[tert-Butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propylamino}-succinic acid dibenzyl ester 
• 99209-23-1 (S)-2-Phenylamino-succinic acid dibenzyl ester 
• 123530-59-6 (S)-2-Diphenylamino-succinic acid dibenzyl ester 
• 116115-34-5 N^α-Boc-L-Arg-(N^ω-9-anthracenesulfonyl)-L-Asp(OBzl)2 
• 97998-29-3 dibenzyl N-<<(diphenylphosphono)methyl>sulfonyl>aspartate 
• 72776-05-7 (S)-benzyl 4-oxoazetidine-2-carboxylate 
• 57618-13-0 Z-Gly-Asp(OBzl)-OBzl 
• 174088-39-2 dibenzyl aspartyl-α-cyanoacetamide 
• 195456-14-5 OC[Asp(OBzl)2]2 

Relevant academic research and scientific papers

The discovery and optimization of benzimidazoles as selective NaV1.8 blockers for the treatment of pain

The voltage gated sodium channel NaV1.8 has been postulated to play a key role in the transmission of pain signals. Core hopping from our previously reported phenylimidazole leads has allowed the identification of a novel series of benzimidazole NaV1.8 blockers. Subsequent optimization allowed the identification of compound 9, PF-06305591, as a potent, highly selective blocker with an excellent preclinical in vitro ADME and safety profile.

Tunable Aggregation-Induced Multicolor Emission of Organic Nanoparticles by Varying the Substituent in Naphthalene Diimide

In this article, we have designed l-aspartic acid-linked naphthalene diimide (NDI)-based amphiphilic molecules having a benzyl ester group at both the terminals with varying substituents (NAB-1-5). The substituent was judiciously modified from an electron-withdrawing group (EWG) like nitrobenzene to an electron-donating group (EDG), methoxybenzene, and finally to an extended aromatic residue (naphthalene) to regulate the π-electron density at the terminal of NDI derivatives. All of the synthesized NDI derivatives were molecularly dissolved in dimethyl sulfoxide (DMSO), and with an increase in the water content within the DMSO solution, the NDI derivative starts to get self-assembled through J-aggregation at and above 40% water content. Self-assembled spherical organic nanoparticles formed in 99% water in DMSO (fw = 99%) were characterized by microscopic studies. All of the NDI derivatives showed very weak emission in the molecularly dissolved state (DMSO). Aggregation-induced emission (AIE) was observed for the NDI derivatives (except NAB-1) at the self-assembled state through excimer formation. Upon excitation at 350 nm, the emission maxima of these NDI-based AIE luminogens (AIE-gens) (NAB-2-5) get red shifted from 463 to 588 nm upon altering the substitution from EWG to EDG at the donor site. Inclusion of proper donor-acceptor moieties in the molecular backbone of the self-assembling unit can govern the AIE in combination with the intramolecular charge-transfer process. Consequently, the emission color of these AIE-gens (NAB-2-5) gets tuned from cyan blue to faint green to strong green and finally to bright orange. The tunable aggregation-induced multicolor emission was investigated by different spectroscopic techniques. These cytocompatible, multicolor-emitting fluorescent organic nanoparticles were utilized for bioimaging applications.

Stereoselective Synthesis of Tricyclic Diproline Analogues that Mimic a PPII Helix: Structural Consequences of Ring-Size Variation

Polycyclic proline-derived scaffolds (ProMs) have recently demonstrated their value as conformationally defined dipeptide analogs for the modular construction of secondary structure mimetics, specifically interfering with PPII helix-mediated protein-protein interactions. We disclose the stereoselective synthesis of two new tricyclic amino acid scaffolds (ProM-4 and ProM-8) that differ from the first generation scaffold ProM-1 by the size of ring A. Conformational preferences and subtle structural differences of the three homologous scaffolds were analyzed by X-ray crystallography, computational calculations, and NMR spectroscopy. N-tert-butoxycarbonyl(Boc)-3-(1-propenyl)azetidine-2-carboxylic acid was prepared from L-aspartic acid through β-lactam intermediates. The corresponding piperidine-based building block rac-N-Boc-3-vinylpipecolic acid was synthesized by Cu-catalyzed 1,4-addition of vinyl-MgBr to methyl N-Boc-2,3-dehydropipecolate. Target molecules were prepared through peptide coupling of the respective ring A building blocks with cis-5-vinylproline tert-butyl ester and subsequent ring-closing metathesis. Selective deprotection of a tert-butyl carbamate (N-Boc protecting group) in the presence of a tert-butyl ester was achieved with trifluoroacetic acid at 0 C. Two new tricyclic amino acid scaffolds, which differ from the first generation scaffold by the size of ring A, were stereoselectively synthesized. The conformational analysis of the three homologous scaffolds was revealed by NMR spectroscopy.

Syntheses of hydroxamic acid-containing bicyclic β-lactams via palladium-catalyzed oxidative amidation of alkenes

Palladium-catalyzed oxidative amidation has been used to synthesize hydroxamic acid-containing bicyclic β-lactam cores. Oxidative cleavage of the pendant alkene provides access to the carboxylic acid in one step.

Organogels and liquid crystalline properties of amino acid-based dendrons: A systematic study on structure-property relationship

Self-assembly behaviors of a series of amino acids-based dendrons, from the first generation (G1) to the third generation (G3) with various focal moieties or peripheral groups, were systematically studied. The supramolecular structures in organogels, thermotropic and lyotropic liquid crystals (LCs) were measured. The influence of the focal groups, dendritic branches, and generation numbers on the mesophase of organogels or LCs was studied by a combination of experimental techniques including transmission electronic spectrometry (TEM), atomic force microscopy (AFM), infrared (IR) spectra, wide-angle X-ray diffraction (WAXD), and small-angle X-ray scattering (SAXS). It was found that the gelation ability of the dendrons in organic solvents was highly related to the generation; namely, none of the G1 dendrons could form organogels, G2 dendrons displayed good gelation ability, and G3 dendrons gelled the organic solvents with the lowest critical gelation concentration. Oscillatory shear measurements indicated that the gels behaved as viscoelastic materials with good tolerance to external shear force. In addition, all of G3 dendrons and some G2 dendrons were capable of self-organizing to afford the thermotropic and lyotropic LCs.

A class of novel conjugates of substituted purine and Gly-AA-OBzl: Synthesis and evaluation of orally analgesic activity

Aimed at the chemotherapy of chronic pain two kinds of analgesic pharmacophores, substituted purine and Gly-AA-OBzl, were coupled via a five-step-reaction procedure and 19 novel conjugates N-[2-chloro-9- (tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters were provided. On mouse-tail flick model their in vivo analgesic activities were assayed. The results indicate that introducing Gly-OC2H 5 into the 6-position of the substituted purine leads to ambiguous increase of the analgesic activity, while introducing Gly-AA-OBzl into this position leads to significant increase of the analgesic activity.

Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

KETOPIPERAZINE DERIVATIVES AS BRADYKININ ANTAGONISTS

Ketopiperazine derivatives are bradykinin B1 antagonists or inverse agonists useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway.

PEPTIDYL DERIVATIVES AS INHIBITORS OF PRO-APOPTOTIC CYSTEINE PROTEINASES

Compounds having the formula I:R 1 COAA. sup.1 AA. sup.2 AA 3 NHYare inhibitors of apopain, an enzyme involved in the process of apoptosis. These compounds are useful as research tools as well as in the treatment of any condition in which reduced apoptosis would be beneficial, including immune deficiency syndromes (including AIDS), type I diabetes, pathogenic infections, cardiovascular and neurological injury, alopecia, aging, Parkinson's disease and Alzheimer's disease.

Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.