2791-84-6

Basic information

• Product Name: L-Glutamic acid dibenzyl ester 4-toluenesulfonate
• Synonyms: GLU(OBZL)-OBZL TOS;GLUTAMIC ACID(OBZL)-OBZL P-TOSYLATE;H-GLU(OBZL)-OBZL 4-TOSYLATE;H-GLU(OBZL)-OBZL P-TOSYLATE;H-GLU(OBZL)-OBZL TOS;H-GLU(OBZL)-OBZL TOSOH;L-GLUTAMIC ACID GAMMA-BENZYL ESTER ALPHA-BENZYL ESTER TOSYLATE;L-GLUTAMIC ACID ALPHA,GAMMA-DIBENZYL ESTER 4-TOLUENESULFONATE SALT
• CAS NO: 2791-84-6
• Molecular Formula: C₇H₈O₃S*C₁₉H₂₁NO₄
• Molecular Weight: 499.58
• EINECS: 220-522-4
• Product Categories: Amino Acids Derivatives;Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Amino Acids and Derivatives
• Mol File: 2791-84-6.mol

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 453.5 °C at 760 mmHg
• Flash Point: 165.6 °C
• Appearance: /Powder
• Vapor Pressure: 2.06E-08mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(2791-84-6)
• EPA Substance Registry System: L-Glutamic acid dibenzyl ester 4-toluenesulfonate(2791-84-6)

Safety Data

• Hazardous Substances Data: 2791-84-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
L-Glutamic acid dibenzyl ester 4-toluenesulfonate is used as a protecting group for carboxylic acids during the synthesis of peptides. It provides stability to the carboxylic acid moiety and prevents unwanted reactions, ensuring the successful formation of the desired peptide sequence.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, L-Glutamic acid dibenzyl ester 4-toluenesulfonate is employed as a protecting group for carboxylic acids in the synthesis of various organic compounds. Its use facilitates the production of complex molecules with specific functional groups, contributing to the development of new drugs and therapeutic agents.
Used in Material Science:
L-Glutamic acid dibenzyl ester 4-toluenesulfonate also finds application in material science, where it is utilized in the synthesis of novel materials with unique properties. Its role as a protecting group for carboxylic acids allows for the controlled formation of complex structures, enabling the development of advanced materials for various applications.

InChI:InChI=1/C19H21NO4.C7H8O3S/c20-17(19(22)24-14-16-9-5-2-6-10-16)11-12-18(21)23-13-15-7-3-1-4-8-15;1-6-2-4-7(5-3-6)11(8,9)10/h1-10,17H,11-14,20H2;2-5H,1H3,(H,8,9,10)/t17-;/m0./s1

Upstream product

• 56-86-0 L-glutamic acid 
• 100-51-6 benzyl alcohol 
• 6893-26-1 D-Glutamic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 61570-89-6 N-Boc-glycyl-L-glutamic acid dibenzyl ester 
• 128164-22-7 BOC-D-Asp(OBzl)-Glu(OBzl)-OBzl 
• 89092-61-5 N-tertbutyloxycarbonyl dipeptide of benzyl glutamate 
• 156078-80-7 (S)-2-{4-[Bis-(2-chloro-ethyl)-amino]-phenoxycarbonylamino}-pentanedioic acid dibenzyl ester 
• 194980-10-4 (S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 330955-09-4 (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester 
• 842120-73-4 dibenzyl [1-(benzyloxycarbonylamino)cyclohexyl]carbonyl-L-prolyl-L-glutamate 
• 842120-64-3 dibenzyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolyl-L-glutamate 
• 900159-03-7 2-allyl-N-Boc-L-Pro-Glu(OBn)-OBn 
• 176448-92-3 N-tert-butoxycarbonyl-L-phenylalanine-L-glutamate dibenzykester 
• 1105050-22-3 N-benzyloxycarbonyl-L-phenylalanine-L-glutamate dibenzylester 
• 1105050-76-7 N-tert-butoxycarbonyl-L-tryptophan-D-glutamate dibenzyllester 
• 1105050-68-7 N-tert-butoxycarbonyl-L-2-naphthylalanine-L-glutamate dibenzylester 

Relevant articles and documents

p-Toluenesulfonyl Chloride Catalysed Facile Synthesis of O-benzyl-l-amino Acids and Their In Vitro Evaluation

Protection and subsequent deprotection of amino acid functional groups play a key role in regioselective peptide synthesis. For protection, carboxylic acid functional groups are often benzylated using p-toluenesulfonic acid catalysed Fischer-Speier esterification reaction. Such reaction involves in situ water formation, which requires subsequent separation by azeotropic distillation for forward shift of equilibrium. To eliminate the need of this corresponding step requiring additional set-up, current study investigated p-toluenesulfonyl chloride as a reasonable alternative catalyst for facile benzylation of selected mono- and di- carboxylic amino acids. Literature reports that p-toluenesulfonyl chloride not only has a better shelf life but also demonstrates better safety in case of accidental systemic absorption over p-toluenesulfonic acid. As the O-benzyl-l-amino acids are often retained without deprotection to constitute the pharmaceutical peptide systems, synthesized compounds were investigated for their biocompatibility using in vitro cytotoxicity assays.

Synthesis and structure reassignment of malylglutamate, a recently discovered earthworm metabolite

Malylglutamate, a newly identified metabolite in earthworms, was synthesized using a traditional peptide coupling approach for assembling the amide from protected malate and glutamate precursors. The proposed structure (1) and a diastereomer were synthesized, but their NMR spectra did not match the natural sample. Further analysis of the natural sample using HMBC spectroscopy suggested an alternative attachment of the malyl moiety, and β-malylglutamate (2) diastereomers were synthesized, L,L-2 and D,D-2. NMR spectra were an excellent match with the natural sample, and chiral-phase chromatography was employed to identify (a)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.

CONJUGATES OF WATER SOLUBLE POLYMER-AMINO ACID OLIGOPEPTIDE-DRUG, PREPARATION METHOD AND USE THEREOF

A conjugate of water soluble polymer-amino acid oligopeptide-drug of Formula (I) below and a pharmaceutical composition comprising the conjugate are provided. In the conjugate, P is a water soluble polymer; X is a linking group, wherein the linking group links P and A1; each of A1, A2 and A3 is independently same or different amino acid residue or amino acid analogue residue; each of D1 and D2 is independently same or different drug molecule residue; a is 0 or 1; b is an integer of 2-12; c is an integer of 0-7; d is 0 or 1. The conjugate could improve drug load capacity, water solubility, stability and activity of the drug.

The discovery of a facile access to the synthesis of NSAID dendritic prodrugs

An efficient and straightforward method for the preparation of dendritic prodrugs is reported. Based on this new approach, a class of biodegradable dendrimers has been synthesised from L-tartaric acid and one of the nonsteroidal anti-inflammatory drugs, namely, aspirin or ibuprofen Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin Universit ,Tianjin 300072, P. R. China.

Synthesis of NO-NSAID dendritic prodrugs via Passerini reaction:new approach to the design of dendrimer-drug conjugates

We report the synthesis of a novel class of dendritic prodrugs via Passerini reaction in one pot. Such dendrimers feature a simultaneous attachment of a conventional non-steroidal anti-inflammatory drug (NSAID) (such as ibuprofen and aspirin) and a nitric oxide (NO)-releasing moiety (such as an organic nitrate) onto their surface, and are therefore regarded as new drug delivery systems for NO-releasing NSAIDs (NO-NSAIDs).

Inhibitors for bacterial cell-wall recycling

Gram-negative bacteria have evolved an elaborate process for the recycling of their cell wall, which is initiated in the periplasmic space by the action of lytic transglycosylases. The product of this reaction, β-d-N- acetylglucosamine-(1a?'4)-1,6-anhydro-β-d-N-acetylmuramyl-l- Ala-I-d-Glu-meso-DAP-d-Ala-d-Ala (compound 1), is internalized to begin the recycling events within the cytoplasm. The first step in the cytoplasmic recycling is catalyzed by the NagZ glycosylase, which cleaves in a hydrolytic reaction the N-acetylglucosamine glycosidic bond of metabolite 1. The reactions catalyzed by both the lytic glycosylases and NagZ are believed to involve oxocarbenium transition species. We describe herein the synthesis and evaluation of four iminosaccharides as possible mimetics of the oxocarbenium species, and we disclose one as a potent (compound 3, Ki = 300 A± 15 nM) competitive inhibitor of NagZ.

Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling

The discovery of peroxisome proliferator-activated receptor γ (PPARγ) antagonists (also termed "selective PPARγ modulators, SPPARγM") is now of a great interest in the treatment of diabetes and obesity. The structure of compound 1a (G3335, Fig. 1), a novel class of PPARγ antagonist, is entirely different from that of other reported PPARγ antagonists. A series of 35 novel analogues (1b-l, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of 1a were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPARγ antagonistic activities (IC50 values of 5.2-25.8 μM) against 10 μM rosiglitazone in the promotion of the PPARγ-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented.

The synthesis of pyrimidin-4-yI substituted a-amino acids. a versatile approach from alkynyl ketones

The reaction of amidines with a-amino acid alkynyl ketones is shown to be a versatile route to pyrimidin-4-yl substituted a-amino acids. This route is also applicable to a parallel synthesis approach and has allowed the formation of a range of pyrimidin-4-yl substituted a-amino acids, including the naturally occurring a-amino acid L-lathyrine 4.