63648-73-7

Basic information

• Product Name: Z-D-GLU-OH
• Synonyms: N-Cbz-D-glutamicacid,98+%;N-CBZ-D-GLU-OH;Z-D-GLU;CBZ-D-GLUTAMIC ACID;Z-D-GLUTAMIC ACID extrapure;(R)-2-(Benzyloxycarbonylamino)-3-(carboxymethyl)propionic acid;2-Phenylmethoxycarbonylaminopentanedioic acid;N-Cbz-D-glutamic Acid Z-D-Glu-OH
• CAS NO: 63648-73-7
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.26
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 63648-73-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 120 °C
• Boiling Point: 529.1 ºC at 760 mmHg
• Flash Point: 273.8 ºC
• Appearance: /
• Density: 1.36 g/cm³
• Refractive Index: 7.5 ° (C=8, AcOH)
• Storage Temp.: Store at RT.
• Solubility: almost transparency in Methanol
• PKA: 3.81±0.10(Predicted)
• CAS DataBase Reference: Z-D-GLU-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-GLU-OH(63648-73-7)
• EPA Substance Registry System: Z-D-GLU-OH(63648-73-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 63648-73-7(Hazardous Substances Data)

Usage

Description

Z-D-GLU-OH, also known as N-Cbz-D-glutamic acid, is an N-Cbz-protected form of D-Glutamic acid. D-Glutamic acid is an unnatural isomer of L-Glutamic acid and is found in bacterial cell wall peptidoglycan of both gram-positive and gram-negative bacteria. It also occurs as poly-gamma-Glutamic acid, which is a weak immunogen but can act as a hapten. Z-D-GLU-OH is a white powder in its chemical form.

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

Downstream Products

• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic 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 
• 135263-61-5 diphenacyl benzyloxycarbonylglutamate 
• 6948-48-7 N-benzyloxycarbonyl-D-glutamic acid dihydrazide 

Relevant articles and documents

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

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.

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.