861658-15-3

Usage

Chemical class

Amino dicarboxylic acids and derivatives

Molecular weight

229.29 g/mol

Appearance

Colorless to pale yellow solid or liquid

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetonitrile

Melting point

Not readily available, but likely to be low due to the presence of flexible carbon chain

Boiling point

Not readily available, but likely to be relatively high due to the presence of multiple functional groups

Density

Not readily available, but likely to be less than 1 g/cm3 due to the presence of a carbon chain

Functional groups

Carboxylic acid, amino, and t-butoxycarbonyl protecting group

Reactivity

Reacts with various reagents to form peptide and protein derivatives

Applications

Organic synthesis
Preparation of peptide and protein derivatives
Production of pharmaceuticals, agrochemicals, and other fine chemicals
Potential applications in medicine and biochemistry due to structural similarity to natural amino acids and ability to modify peptide and protein properties

Safety

Handle with care, as it may be harmful if inhaled, ingested, or if it comes into contact with the skin

Storage

Store in a cool, dry, and well-ventilated area, away from heat, sparks, and open flames

Stability

Stable under normal conditions, but may decompose upon exposure to heat, light, or moisture

Regulatory status

Not readily available, but it may be subject to specific regulations depending on its intended use and concentration in a given product.

Upstream product

• 186581-53-3 diazomethane 
• 2419-94-5 Boc-Glu 
• 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 
• 4976-88-9 (S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate 
• 206128-03-2 (S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate 
• 56-85-9 L-glutamine 
• 74-88-4 methyl iodide 
• 75-77-4 chloro-trimethyl-silane 
• 16422-27-8 1,5-dimethyl (2R)-2-aminopentanedioate 
• 6893-26-1 D-Glutamic acid 
• 861657-91-2 rac-1-(tert-butyl) 2-methyl 5-oxopyrrolidine-1,2-dicarboxylate 

Downstream Products

• 84590-48-7 indolactam V 
• 1260509-73-6 C₁₃H₂₁NO₄ 
• 1157849-50-7 C₆H₁₄N₂*(x)ClH 
• 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 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 

Relevant academic research and scientific papers

[1,2] Boc migration during pyroglutamate alkylations

Treatment of N-Boc protected pyroglutamates with strong bases lead to a Boc migration from the N-atom to the C2 position when no or poor electrophiles are being used.

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.

L-glutamic acid derivative and synthesis method and application thereof

The invention belongs to the technical field of synthesis of medical and traditional Chinese medicine intermediates, and discloses an L-glutamic acid derivative and a synthesis method and applicationthereof. All the steps in the synthesis method are simple and in order , the obtained L-dimethyl glutamate hydrochloride oily matter is directly put into the next step of reaction through a one-pot method, L-dimethyl glutamate hydrochloride solids do not need to be obtained, the use of all the raw materials can be effectively reduced, and the cost is reduced; ethyl acetate is selected as a reaction solvent and can be effectively recycled, the utilization rate of the ethyl acetate is remarkably increased, and pollution to the environment is reduced; a final product is obtained in a crystallization manner so that the convenience and the storage convenience during transportation are improved, and the quality and the yield of the product can be further improved. The technical scheme of the synthesis method is complete and simple, the produced product is high in crystallization yield and better in quality, the overall yield of the product is conveniently, rapidly, scientifically and effectively increased to 85% or above, and raw materials are provided for research and development of new drugs.

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.

Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family

Natural products (NPs) are an important inspirational source for developing drugs and chemical probes. In 1999, the group of ōmura reported the constitutional elucidation of zelkovamycin. Although largely unrecognized so far, this NP displays structural s

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).

[...] compound for the preparation of a classical swine fever virus (ASFV) infection drug application (by machine translation)

The invention relates to peptide aldehyde compound I, compound II in preparation for treating swine fever virus (ASFV) infection the application of the medicament, and it also relates to various optical isomer, a pharmaceutically acceptable solvate and pr

Preparation and uses of novel Michael receptor-based enterovirus 71 type inhibitor

The present invention relates to a class of novel Michael receptor-based virus 71 (EV71) 3C protease inhibitors, wherein various variables of the structure general formula (M) are defined in the specification, and the compounds effectively inhibit or block the replication of enterovirus 71. The present invention relates to discovery and applications of the compound containing the structure generalformula (M), various optical isomers, pharmaceutically active metabolites, pharmaceutically acceptable salts, solvates and prodrugs thereof in preparation of antiviral drugs for the treatment of hand-foot-mouth virus infection diseases. The invention relates to an intermediate and a synthesis method for preparing the compound having the structure general formula (M). The formula (M) is defined inthe specification.

Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

The invention relates to a synthetic process of an anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride. The synthetic process comprises the steps: using inexpensive L-glutamic acid as a starting material, and performing esterification, amino protection, reduction, hydroxyl protection, substitution, cyclization and removal of protecting groups for amino groups so as to obtainthe R-3-amino-piperidine dihydrochloride. Compared with the prior art, the synthetic process has cheap and easily available raw materials, good selectivity, good atomic economy, high total yield and mild reaction conditions, and is suitable for industrial production.

TRICYCLIC COMPOUNDS AS HISTONE METHYL-TRANSFERASE INHIBITORS

The present disclosure provides certain tricyclic compounds that are histone methyltransferases G9a and/or GLP inhibitors and are therefore useful for the treatment of diseases treatable by inhibition of G9a and/or GLP such as cancers and hemoglobinopathi