30924-93-7

Basic information

• Product Name: Boc-L-Glutamic acid 1-benzyl ester
• Synonyms: N-Boc-D-glutamic acid 1-benzyl ester, 99%;N-(tert-butoxycarbonyl)-L-glutamic acid alpha-benzyl ester;N-(Tert-butoxycarbonyl)-l-glutamic acid 1-be;L-GlutaMic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 1-(phenylMethyl) ester;1-Benzyl N-Boc-L-glutamate N-Boc-L-glutamic Acid 1-Benzyl Ester N-(tert-Butoxycarbonyl)-L-glutamic Acid 1-Benzyl Ester Boc-Glu-OBzl;α-benzyl Nα-(tert-butyloxycarbonyl)-L-glutaMate;N-Boc-L-glutamic Acid α-Benzyl Ester;Boc-Glu-OBzl (cryst) Novabiochem
• CAS NO: 30924-93-7
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.37
• Product Categories: Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;peptide;Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E]
• Mol File: 30924-93-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 95.0 to 99.0 °C
• Boiling Point: 522.6 °C at 760 mmHg
• Flash Point: 269.859 °C
• Appearance: /
• Density: 1.198 g/cm³
• Vapor Pressure: 9.49E-12mmHg at 25°C
• Refractive Index: -30 ° (C=0.7, MeOH)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.48±0.10(Predicted)
• BRN: 2482076
• CAS DataBase Reference: Boc-L-Glutamic acid 1-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-Glutamic acid 1-benzyl ester(30924-93-7)
• EPA Substance Registry System: Boc-L-Glutamic acid 1-benzyl ester(30924-93-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 30924-93-7(Hazardous Substances Data)

Usage

Description

Boc-L-Glutamic acid 1-benzyl ester, also known as Boc-Glu-OBzl, is an amino acid building block with a white solid appearance. It is a derivative of L-glutamic acid, featuring a benzyl ester group and a Boc-protecting group. Boc-L-Glutamic acid 1-benzyl ester is widely utilized in the synthesis of various peptides and has been particularly noted for its enzyme inhibitory activity in vitro.

Uses

Used in Pharmaceutical Research:
Boc-L-Glutamic acid 1-benzyl ester is used as a monopeptide for studying the interaction of nucleic acid bases with peptides. This application is crucial in understanding the molecular mechanisms underlying various biological processes and can contribute to the development of novel therapeutic strategies.
Used in Enzyme Research:
Boc-L-Glutamic acid 1-benzyl ester serves as an effective substrate for vitamin K-dependent carboxylase, an enzyme that plays a vital role in the post-translational modification of specific proteins. This application is essential for research on the enzyme's function, regulation, and potential as a therapeutic target.
Used in Synthesis of Peptide-based Inhibitors:
Boc-L-Glutamic acid 1-benzyl ester is used as an amino acid building block in the synthesis of peptide-based inhibitors targeting human caspases and human rhinovirus (HRV) 3C protease. These inhibitors exhibit enzyme inhibitory activity in vitro, making them valuable tools in the development of new antiviral and anti-apoptotic drugs.
Used in Chemical Synthesis:
As an amino acid building block, Boc-L-Glutamic acid 1-benzyl ester is employed in the synthesis of various peptides and peptide derivatives. Its unique structure allows for the creation of diverse peptide sequences with potential applications in pharmaceuticals, diagnostics, and research.

InChI:InChI=1/C17H23NO6/c1-17(2,3)24-16(22)18-13(9-10-14(19)20)15(21)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,19,20)/t13-/m1/s1

Upstream product

• 617-65-2 Glutamic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 501-53-1 benzyl chloroformate 
• 2419-94-5 Boc-Glu 
• 100-51-6 benzyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13030-09-6 1-benzyl L-glutamate 
• 30924-91-5 dicyclohexylamine salt of α-benzyl Boc-glutamate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 31874-50-7 Boc-Gln(Dmb)-OBzl 
• 78658-49-8 Boc-Glu(OSu)-OBn 
• 87174-84-3 (S)-2-tert-Butoxycarbonylamino-5-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-5-hydroxy-pentanoic acid benzyl ester 
• 91229-92-4 α-benzyl N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamate 
• 37787-77-2 Boc-L-proline benzyl ester 
• 91229-97-9 (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester 
• 105589-11-5 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester 
• 72468-46-3 N²-(tert-butyloxycarbonyl)-N⁵,N⁵-dimethylglutamine benzyl ester 
• 132245-78-4 (S)-2-tert-butoxycarbonylaminopentanedioic acid 1-benzyl ester 5-methyl ester 
• 148529-07-1 (S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid 
• 370867-50-8 benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate 
• 370867-51-9 Boc-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr-OMe 
• 848780-48-3 Troc-(S)-Thr[Boc-(S)-Phs(Bn)-(S)-Phe-(S)-NMe-Tyr-(S)-Ile]-(S)-Phe-OAllyl 
• 370867-66-6 phosphoric acid dibenzyl ester 2-benzyloxy-2-[2,15-dibenzyl-8-sec-butyl-21-hydroxy-5-(4-hydroxy-benzyl)-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaaza-bicyclo[16.3.1]docos-12-ylcarbamoyl]-ethyl ester 

Relevant articles and documents

Diazaphosphinyl radical-catalyzed deoxygenation of α-carboxy ketones: A new protocol for chemo-selective C-O bond scission: Via mechanism regulation

C-O bond cleavage is often a key process in defunctionalization of organic compounds as well as in degradation of natural polymers. However, it seldom occurs regioselectively for different types of C-O bonds under metal-free mild conditions. Here we report a facile chemo-selective cleavage of the α-C-O bonds in α-carboxy ketones by commercially available pinacolborane under the catalysis of diazaphosphinane based on a mechanism switch strategy. This new reaction features high efficiency, low cost and good group-tolerance, and is also amenable to catalytic deprotection of desyl-protected carboxylic acids and amino acids. Mechanistic studies indicated an electron-transfer-initiated radical process, underlining two crucial steps: (1) the initiator azodiisobutyronitrile switches originally hydridic reduction to kinetically more accessible electron reduction; and (2) the catalytic phosphorus species upconverts weakly reducing pinacolborane into strongly reducing diazaphosphinane. This journal is

Ready protease-catalyzed synthesis of carbohydrate-amino acid conjugates.

The protease-catalyzed synthesis of amino acid est-carbohydrate conjugates as glycopeptide analogues has been achieved in a highly regioselective and carbohydrate-specific manner using amino acid vinyl ester acyl donors and minimally or completely unprotected carbohydrate acyl acceptors, which together probed active sites of proteases to reveal yield efficiencies that are modulated by the carbohydrate C-2 substitutent, and that may be exploited to allow selective one-pot syntheses.

A study of the delivery-targeting concept applied to antineoplastic drugs active on human osteosarcoma. I. Synthesis and biological activity in nude mice carrying human osteosarcoma xenografts of gem-bisphosphonic methotrexate analogues

With the aim of verifying the concept of osteotic vectorisation, synthesis of three methotrexate (MTX) gem-diphosphonic analogues (compounds A, B and C) was performed. These molecules were tested on BALB/c and NIH III mice previously grafted with subcutaneous implants of OHS, TTX p7 and/or TTX p11 human osteosarcoma cell lines. Antineoplasic activity of compound B and C (active compounds) was compared to the activity for MTX alone and to activity of compound A (inactive compound). Compounds B and C exhibited an increased antineoplasic activity compared to MTX alone and to compound A. At equimolar doses, compound B was found to be 5-6-fold more active than MTX given alone. We have discussed the concept of osteotic vectorisation of compound B, which could be regarded as a prodrug.