59279-60-6

Basic information

• Product Name: (R)-N-Boc-glutamic acid-1,5-dimethyl ester
• Synonyms: BOC-L-GLU(OME)-OME;BOC-L-GLUTAMIC ACID DIMETHYL ESTER;BOC-GLU(OME)-OME;N-alpha-t-Butyloxycarbonyl-L-glutamic acid di-methyl ester;Dimethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate;(S)-diMethyl 2-(tert-butoxycarbonylaMino)pentanedioate;(S)-2-tert-ButoxycarbonylaMinopentanedioic acid diMethyl ester;N-Boc-L-GlutaMic Acid diMethyl ester/(S)-2-tert-ButoxycarbonylaMino-pentanedioic acid diMethyl ester (S)-2-tert-ButoxycarbonylaMino-pentanedioic acid diMethyl ester
• CAS NO: 59279-60-6
• Molecular Formula: C₁₂H₂₁NO₆
• Molecular Weight: 275.3
• Mol File: 59279-60-6.mol
• Article Data: 62

Chemical Properties

• Melting Point: 43.0 to 47.0 °C
• Boiling Point: 370.9 °C at 760 mmHg
• Flash Point: 178.1 °C
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.117g/cm³
• Vapor Pressure: 1.07E-05mmHg at 25°C
• Refractive Index: 1.452
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 10.86±0.46(Predicted)
• CAS DataBase Reference: (R)-N-Boc-glutamic acid-1,5-dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Boc-glutamic acid-1,5-dimethyl ester(59279-60-6)
• EPA Substance Registry System: (R)-N-Boc-glutamic acid-1,5-dimethyl ester(59279-60-6)

Safety Data

• Hazardous Substances Data: 59279-60-6(Hazardous Substances Data)

Usage

Uses

(R)-N-Boc-glutamic acid-1,5-dimethyl ester can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development and chemical production processes.

Synthesis

L-glutamic acid (10.0 g, 67.97 mmol) was dissolved in 200 mL of methanol, and SOCl2(10.85 mL, 149.53 mmol)was slowly added dropwise under an ice bath. After the addition, reflux was performed at 65 ° C. After 2 hours, the reaction system was cooled to room temperature, and methanol was evaporated to dryness under reduced pressure to obtain a colorless viscous substance.This colorless viscous substance was dissolved in 200 mL of THF, (Boc)2O (22.25 g, 101.95 mmol) was addedunder an ice bath, and triethylamine (14.13 mL, 101.95 mmol) was slowly added dropwise.After the addition was complete, the reaction was allowed to proceed at room temperature overnight.After completion of the reaction, the solvent was distilled off under reduced pressure.The residue was dissolved in 200 mL of dichloromethane.The organic phase was washed with water (200 mL * 2), saturated citric acid solution (200 mL * 2), saturated sodium bicarbonate solution (200 mL * 2), and saturated brine (200 mL * 2) in that order.The organic phase was dried over anhydrous Na2SO4. Thefiltrate was collected by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 4: 1 v / v) to give a colorless oily product 2 (18.34 g, yield 98%)

InChI:InChI=1/C12H21NO6/c1-12(2,3)19-11(16)13-8(10(15)18-5)6-7-9(14)17-4/h8H,6-7H2,1-5H3,(H,13,16)/t8-/m0/s1

Upstream product

• 67-56-1 methanol 
• 56-86-0 L-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 75-77-4 chloro-trimethyl-silane 
• 2419-94-5 Boc-Glu 
• 74-88-4 methyl iodide 
• 13726-85-7 Boc-Gln-OH 
• 56-85-9 L-glutamine 
• 67436-17-3 dimethyl (S)-N-(benzyloxycarbonyl)glutamate 
• 23150-65-4 L-glutamic dimethyl ester hydrochloride 
• 500143-66-8 dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate 
• 206128-03-2 (S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate 
• 4976-88-9 (S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate 

Downstream Products

• 431881-22-0 (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester 
• 500143-66-8 dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate 
• 869494-44-0 (E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-hydroxy-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 869494-40-6 (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 869494-42-8 (E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 328086-61-9 ethyl (S,E)-4-((tert-butoxycarbonyl)amino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 
• 1157849-50-7 C₆H₁₄N₂*(x)ClH 
• 307532-02-1 C₁₂H₁₈N₂*(x)ClH 
• 122380-18-1 iso-thaxtomin A 
• 122380-18-1 thanxtomin-A 
• 1333536-82-5 (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 13734-28-6 Boc-Lys-OH 
• 365973-28-0 (2S,3aS,7aR)-7a-allyl-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 

Relevant articles and documents

Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

Selenolysine: A New Tool for Traceless Isopeptide Bond Formation

Despite their biological importance, post-translationally modified proteins are notoriously difficult to produce in a homogeneous fashion by using conventional expression systems. Chemical protein synthesis or semisynthesis offers a solution to this problem; however, traditional strategies often rely on sulfur-based chemistry that is incompatible with the presence of any cysteine residues in the target protein. To overcome these limitations, we present the design and synthesis of γ-selenolysine, a selenol-containing form of the commonly modified proteinogenic amino acid, lysine. The utility of γ-selenolysine is demonstrated with the traceless ligation of the small ubiquitin-like modifier protein, SUMO-1, to a peptide segment of human glucokinase. The resulting polypeptide is poised for native chemical ligation and chemoselective deselenization in the presence of unprotected cysteine residues. Selenolysine's straightforward synthesis and incorporation into synthetic peptides marks it as a universal handle for conjugating any ubiquitin-like modifying protein to its target.

Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers

Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).