1155-62-0

Basic information

• Product Name: N-Cbz-L-glutamic acid
• Synonyms: n-[(phenylmethoxy)carbonyl]-l-glutamicaci;Z-L-GLUTAMIC ACID extrapure;N-(Carbobenzyloxy)-L-glutamic acid, Z-L-Glutamic acid;(2S)-2-(Phenylmethoxycarbonylamino)pentanedioic acid;N-(Benzyloxycarbonyl)glutamic acid;N-BENZYLOXYCARBONYL-L-GLUTAMIC ACID 99%;(2S)-2-(Benzyloxycarbonylamino)glutaric acid;(S)-2-(Benzyloxycarbonylamino)-3-(carboxymethyl)propionic acid
• CAS NO: 1155-62-0
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.26
• EINECS: 214-584-1
• Product Categories: Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Chiral Compounds;Z-Amino acid series;Amino Acids & Derivatives;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Protected Amino Acids;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Glutamic acid [Glu, E]
• Mol File: 1155-62-0.mol

Chemical Properties

• Melting Point: 115-117 °C(lit.)
• Boiling Point: 423.93°C (rough estimate)
• Flash Point: 273.8 °C
• Appearance: off-white solid
• Density: 1.2801 (rough estimate)
• Vapor Pressure: 5.03E-12mmHg at 25°C
• Refractive Index: -7.5 ° (C=8, AcOH)
• Storage Temp.: −20°C
• Solubility: DMF, Methanol
• PKA: 3.81±0.10(Predicted)
• BRN: 2061272
• CAS DataBase Reference: N-Cbz-L-glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-glutamic acid(1155-62-0)
• EPA Substance Registry System: N-Cbz-L-glutamic acid(1155-62-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1155-62-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Cbz-L-glutamic acid is used as a building block for the synthesis of various pharmaceutical compounds. Its role in the synthesis process is crucial, as it can be incorporated into the structure of drugs to enhance their efficacy, stability, or bioavailability.
Used in Synthesis of Carboxyalkyl Peptides:
In the field of biochemistry and drug development, N-Cbz-L-glutamic acid is used as a key component in the synthesis of carboxyalkyl peptides. These peptides serve as inhibitors of the angiotensin-converting enzyme (ACE) found in human blood serum. By inhibiting ACE, these peptides can help regulate blood pressure and are thus valuable in the development of antihypertensive medications.
Used in Organic Synthesis:
N-Cbz-L-glutamic acid is also utilized in organic synthesis for the preparation of various compounds, including those with potential applications in the fields of material science, agrochemicals, and other specialty chemicals. Its versatility and reactivity make it a valuable intermediate in the synthesis of complex organic molecules.

InChI:InChI=1/C13H15NO6/c15-11(16)7-6-10(12(17)18)14-13(19)20-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,19)(H,15,16)(H,17,18)/t10-/m1/s1

Upstream product

• 56-86-0 L-glutamic acid 
• 145080-95-1 (S)-(-)-2-isocyanatoglutaric acid diethyl ester 
• 100-51-6 benzyl alcohol 
• 1634-89-5 Z-(S)-Glu-Gly 
• 89714-94-3 acetic acid-[(25R)-5α-spirosta-7,9(11)-dien-3β-yl ester 
• 4587-40-0 N-(N-benzyloxycarbonyl-α-L-glutamyl)-glycine ethyl ester 
• 908571-04-0 N-[N-(N-benzyloxycarbonyl-α-L-glutamyl)-glycyl]-glycine 
• 501-53-1 benzyl chloroformate 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 5672-83-3 Z-L-GluOMe 
• 988-75-0 N-benzyloxycarbonyl-L-glutamyl-L-tyrosine 
• 25126-07-2 N-(benzyloxycarbonyl)-L-glutamic acid, α-phenyl ester 

Downstream Products

• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 6398-06-7 N-benzyloxycarbonyl-L-isoglutamine 
• 198134-01-9 N²-benzyloxycarbonyl-N¹-phenyl-L-isoglutamine 
• 103156-77-0 Cbz-L-Glu(OBzl)-OBzl 
• 22885-74-1 N,N'(N-benzyloxycarbonyl-glutamoyl)-bis-glycine diethyl ester 
• 49761-26-4 N-benzyloxycarbonyl-L-glutamic acid bis(4-nitrophenyl)ester 
• 4587-40-0 N-(N-benzyloxycarbonyl-α-L-glutamyl)-glycine ethyl ester 
• 65148-67-6 N_.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester 
• 16881-41-7 di-tert-butyl N-Cbz-L-glutamate 
• 95063-62-0 (S)-4-Benzyloxycarbonylamino-5-oxo-5-piperidin-1-yl-pentanoic acid tert-butyl ester 
• 95063-63-1 (S)-2-Benzyloxycarbonylamino-5-oxo-5-piperidin-1-yl-pentanoic acid tert-butyl ester 
• 95063-55-1 (S)-4-Benzyloxycarbonylamino-5-oxo-5-piperidin-1-yl-pentanoic acid 
• 95063-56-2 (S)-2-Benzyloxycarbonylamino-5-oxo-5-piperidin-1-yl-pentanoic acid 
• 95063-64-2 (S)-4-Benzyloxycarbonylamino-5-morpholin-4-yl-5-oxo-pentanoic acid tert-butyl ester 

Relevant articles and documents

Effect of freezing on the enzymatic coupling of specific amino acid-containing peptide fragments

The effect of freezing on the enzymatic coupling of highly specific amino acid-containing peptide fragments was investigated using trypsin, α-chymotrypsin, and Bacillus licheniformis Glu-specific endopeptidase as biocatalysts. Comparison with reactions at normal temperature indicates that freezing efficiently represses the cleavage of specific peptide bonds independent of their individual localisation and specificity achieving irreversible and efficient peptide bond formation without proteolytic side reactions. Copyright (C) 2000 Elsevier Science Ltd.

Preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid

The invention discloses a preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid, which mainly solves the complexity in the original process, and is long in period and high in cost. The method specifically comprises first steps of preparing L - benzyloxycarbonyl N - glutamic acid from - L - glutamic acid and a benzyloxycarbonyl donor, second steps of intramolecular condensation cyclization N - benzyloxycarbonyl - L - glutamic acid to obtain the N -benzyloxycarbonyl - L - glutamic acid crude product. The third The crude N - benzyloxycarbonyl - L - glutamic acid crude product and the organic amine base are mixed, and the organic amine salt form is prepared by the solubility of the product in a solvent, fourth (N -) - L - (benzyloxycarbonyl) S oxopyrrolidine -1 - formic acid is prepared by desalinating -5 - benzyloxycarbonyl -2 - glutamic acid. To the method, the high-purity product is prepared, and the yield and the quality are greatly improved.

PROCESSES FOR PREPARATION OF (S)-TERT-BUTYL 4,5-DIAMINO-5-OXOPENTANOATE

Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.

A method for the preparation of amine to that (by machine translation)

The invention discloses a method for the preparation of amine to that, the specific step includes: to 2 - methyl - 3 - nitro benzoic acid as the raw material, to obtain 2 - bromomethyl - 3 - nitro-benzoic acid methyl ester; L - glutamic acid as the raw material to make the N - CBZ - L - glutamic acid; to N - CBZ - L - glutamic acid as the raw material to make the 3 - amino - 2, 6 - piperidine dione hydrochloride; to 2 - methyl - 3 - nitro-benzoic acid methyl ester with 3 - amino - 2, 6 - piperidine dione hydrochloride as the raw material to make the 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione; to 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione as raw materials to that amine. The method of the invention has simple technological process, raw material economic, few by-products, and purification is simple, high yield, environment-friendly and the like, after treatment is simple, has better practicability and application value, has great industrial prospects. (by machine translation)

Synthesis of fully protected (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxy heptanoic acid

(2R,3R,4S)-4-Amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), a common constituent of biologically active marine peptides, callipeltin A (1) and neamphamide A, was synthesized as its orthogonally protected derivative from L-glutamic acid in 15 steps. Guanidination by the Mitsunobu condition and osmium-catalyzed dihydroxylation of the corresponding Z-olefin were employed as the key steps.

Synthesis and Kinetic Characterisation of Water-Soluble Fluorogenic Acyl Donors for Transglutaminase 2

Small glutamate-containing peptides bearing coumarin derivatives as fluorescent leaving groups attached to the γ-carboxylic acid group of the Glu residue were synthesised and investigated with regard to their potential to act as substrates for transglutam

Synthesis and physicochemical characterization of the impurities of pemetrexed disodium, an anticancer drug

A physicochemical characterization of the process-related impurities associated with the synthesis of pemetrexed disodium was performed. The possibility of pemetrexed impurities forming has been mentioned in literature, but no study on their structure has been published yet. This paper describes the development of the synthesis methods for these compounds and discusses their structure elucidation on the basis of two-dimensional NMR experiments and MS data. The identification of these impurities should be useful for the quality control during the production of the pemetrexed disodium salt.

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.

Synthesis and relaxometric characterization of a MRI Gd-based probe responsive to glutamic acid decarboxylase enzymatic activity

Novel contrast agent based systems, which selectively visualize specific cells, e.g., neurons in the brain, would be of substantial importance for the fast developing field of molecular magnetic resonance imaging (MRI). We report here the synthesis and in vitro validation of a Gd(III)-based contrast agent designed to act as an MRI responsive probe for imaging the activity of the enzyme glutamic acid decarboxylase (GAD) present in neurons. Upon the action of the enzyme, the Gd(III) complex increases its hydration sphere and takes on a residual positive charge that promotes its binding to endogenous macromolecules. Both effects contribute in a synergic way to generate a marked relaxation enhancement, which directly reports enzyme activity and will allow activity detection of GAD positive cells in vitro and in vivo selectively.