63648-73-7

Usage

Uses

Used in Pharmaceutical Industry:
Z-D-GLU-OH is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique properties as an unnatural isomer of L-Glutamic acid. Its presence in bacterial cell wall peptidoglycan makes it a potential target for the development of new antibiotics.
Used in Research and Development:
Z-D-GLU-OH is used as a research compound for studying the differences between Dand L-isomers of amino acids, as well as their roles in biological systems. This can lead to a better understanding of various biological processes and the development of novel therapeutic strategies.
Used in Immunology:
As a weak immunogen capable of acting as a hapten, Z-D-GLU-OH is used in the field of immunology to study immune responses and the development of antibodies. This can contribute to the advancement of vaccine design and the understanding of autoimmune diseases.
Used in Material Science:
The unique properties of Z-D-GLU-OH, such as its ability to act as a hapten, can also be utilized in material science for the development of new materials with specific interactions and properties. This can have applications in various industries, including electronics, coatings, and adhesives.

Upstream product

• 617-65-2 Glutamic acid 
• 501-53-1 benzyl chloroformate 
• 19506-72-0 benzyl-8-quinolyl carbonate 
• 6893-26-1 D-Glutamic acid 
• 51644-83-8 N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester 
• 921-01-7 rac-cysteine 
• 1155-62-0 N-benzyloxycarbonyl-DL-glutamic acid 
• 62-53-3 aniline 
• 204922-65-6 2-Benzyloxycarbonylamino-4-nitro-pentanedioic acid dimethyl ester 
• 204930-93-8 2-Benzyloxycarbonylamino-pentanedioic acid dimethyl ester 

Downstream Products

• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic acid 
• 135263-61-5 diphenacyl benzyloxycarbonylglutamate 
• 19525-56-5 4-(2-CARBOXY-ETHYL)-5-OXO-OXAZOLIDINE-3-CARBOXYLIC ACID BENZYL ESTER 
• 393104-67-1 bis{2-[3,4-bis(undecyloxy)phenyl]ethyl} D,L-glutamate 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 115141-89-4 (4S)-3-(benzyloxycarbonyl)-4-(3-hydroxypropyl)-1,3-oxazolidin-5-one 
• 19522-39-5 (R)-5-amino-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid 
• 26566-11-0 N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester 
• 71869-80-2 benzyl (R)-(2,6-dioxotetrahydro-2H-pyran-3-yl)carbamate 
• 56202-05-2 (R)-4-Benzyloxycarbonylamino-4-dipropylcarbamoyl-butyric acid 
• 106930-50-1 Z-D-Glu-(O-t-Bu)-O-t-Bu 
• 97975-57-0 (4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one 
• 70663-15-9 Z-D-Glu-α-4,4'-Dimethoxybenzhydrylamid 

Relevant academic research and scientific papers

Convergent synthesis of novel muramyl dipeptide analogues: Inhibition of porphyromonas gingivalis-induced pro-inflammatory effects by high doses of muramyl dipeptide

Porphyromonas gingivalis (P.g.)-induced TNF-α can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 μg/mL of MDP (MDP-low) up-regulated TNF-α by 29%, while 100

Total synthesis of (-)-platensimycin by advancing oxocarbenium- and iminium-mediated catalytic methods

(-)-Platensimycin is a potent inhibitor of fatty acid synthase that holds promise in the treatment of metabolic disorders (e.g., diabetes and "fatty liver") and pathogenic infections (e.g., those caused by drug-resistant bacteria). Herein, we describe its total synthesis through a four-step preparation of the aromatic amine fragment and an improved stereocontrolled assembly of the ketolide fragment, (-)-platensic acid. Key synthetic advances include 1) a modified Lieben haloform reaction to directly convert an aryl methyl ketone into its methyl ester within 30 seconds, 2) an experimentally improved dialkylation protocol to form platensic acid, 3) a sterically controlled chemo- and diastereoselective organocatalytic conjugate reduction of a spiro-cyclized cyclohexadienone by using the trifluoroacetic acid salt of α-amino di-tert-butyl malonate, 4) a tetrabutylammonium fluoride promoted spiro-alkylative para dearomatization of a free phenol to assemble the cagelike ketolide core with the moderate leaving-group ability of an early tosylate intermediate, and 5) a bismuth(III)-catalyzed Friedel-Crafts cyclization of a free lactol, with LiClO4 as an additive to liberate a more active oxocarbenium perchlorate species and suppress the Lewis basicity of the sulfonyloxy group. The longest linear sequence is 21 steps with an overall yield of 3.8% from commercially available eugenol. Relay tactics: The stereocontrolled assembly of the potent antibiotic (-)-platensimycin in 21 steps and 3.8% yield from eugenol is described (see scheme; TBAF: tetrabutylammonium fluoride; Ts: toluene-4-sulfonyl). Highlights are 1) a rapid oxidative esterification of an acyl aromatic, 2) a reliable dialkylation protocol to form platensic acid, 3) a π-facial conjugate reduction of a dienone, 4) a TBAF-promoted alkylative dearomatization of a free phenol, and 5) a Friedel-Crafts closure of a free lactol.

Synthesis and anticonvulsant activity of (R)- and (S)-3-(Carbobenzyloxy- amino-1-glutarimidooxy)esters

A series of (R)- and (S)-3-carbobenzyloxy-amino-1-glutarimidooxy-esters (5a-e) ((R)-and (S)-methyl-1-(3-carbobenzyloxy-amino-I glutarimidooxy)acetate (5a), (R)-and (S)-ethyl-1-(3-carbobenzyloxy-amino-glutarimidooxy)acetate (5b), (R)- and (S)-ethyl-1-(3-carbo-benzyloxy-amino-glutarimidooxy)propionate (5c), (R)- and (S)-methyl-2-(3-carbobenzyloxy-amino-glutarimidooxy)butyrate (5d), (R)- and (S)-ethyl-2-(3-carbobenzyloxy-amino-glutarimidooxy)butyrate (5e) were synthesized and investigated their anticonvulsant activities.

Constrained peptidomimetics reveal detailed geometric requirements of covalent prolyl oligopeptidase inhibitors

Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light on the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.

Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers

(Chemical Equation Presented) Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative 4, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.

A novel immunostimulator, N2-[α-O-Benzyl-N-(acetylmuramyl) -L-alanyl-D-isoglutaminyl]-N6-trans-(m-nitrocinnamoyl)-L-lysine, and its adjuvancy on the hepatitis B surface antigen

N2-[α-O-Benzyl-N-(acetylmuramyl)-L-alanyl-D-isoglutaminyl] -N6-trans-(m-nitrocinnamoyl)-L-lysine (muramyl dipeptide C, or MDP-C) has been synthesized as a novel, nonspecific immunomodulator. The present study shows that MDP-C induces

Beta-strand mimetics and method relating thereto

Conformationally constrained compounds which mimic the secondary structure of β-strand regions of biologically active peptides and proteins are disclosed. Such β-strand mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the β-strand mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members.

(2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: Synthesis and duplex/triplex stability

This article reports the design and facile synthesis of novel chiral six-membered PNA analogues (2S,5R/2R,5S)-1-(N-Boc-aminoethyl)-5-(thymin-1-yl) pipecolic acid, aepipPNA IV that upon incorporation into standard aegPNA sequences effected stabilization of

THIAZOLIDINE DERIVATIVES

An object of the present invention is to provide novel thiazolidine derivatives which are useful as drugs. The thiazolidine derivatives according to the present invention are compounds represented by the following general formula [I] and salts thereof, wherein R 1is alkyl, hydroxy, alkoxy, alkoxyalkyl, phenyl, phenylalkyl, phenylalkoxy, phenoxy, phenoxyalkyl, amino, alkylamino or a nonaromatic heterocycle; R 2is H or alkyl; R 3is H, alkyl or phenyl; R 4is H or alkyl; R 5is alkyl, halogenoalkyl, hydroxy, alkoxy, phenyl, phenylalkoxy, phenoxy, carboxyl, alkoxycarbonyl, phenylalkoxycarbonyl or an aromatic heterocycle; A 1is alkylene; and A 2is alkylene.

New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids

Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N,O-protected dehydroalanines derivable from the corresponding alanine, serine and cysteine derivatives by specific routes, the overall procedures provide a means for selective conversion of these simple α-amino acids into more complex ones.