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Boc-DL-Glu(OMe)-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

BOC-Amino Acids

Catalog number

BAT-000801

Molecular Formula

C11H19NO6

Molecular Weight

261.3

Synonyms

4-((tert-Butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid; Boc-DL-glutamic acid a-methyl ester

Storage

Store at 2-8 °C

Boc-DL-Glu(OMe)-OH, a chemical compound frequently utilized in peptide synthesis and pharmaceutical research, boasts diverse applications.

Peptide Synthesis: Serving as a crucial building block in peptide synthesis, Boc-DL-Glu(OMe)-OH plays a pivotal role. Acting as a shielded amino acid derivative, it enables the selective incorporation of glutamic acid residues into peptide chains. This compound safeguards the integrity of the amino acid sequence by averting premature reactions during synthesis, ensuring the peptides produced exhibit the intended structure and functionality.

Pharmaceutical Research: In the realm of pharmaceutical research, Boc-DL-Glu(OMe)-OH emerges as a fundamental component in the creation of peptide-based medicinal agents. It facilitates the synthesis of peptides with therapeutic relevance, capable of targeting specific receptors or enzymes within the body. Through the utilization of this protected amino acid, researchers can craft stable peptide analogs boasting heightened bioavailability and efficacy, fostering the emergence of novel drug candidates.

Enzyme Inhibition Studies: Employed in investigations pertaining to enzyme inhibition, Boc-DL-Glu(OMe)-OH serves as a valuable tool for exploring the interaction between peptides and catalytic sites. By methodically integrating Boc-DL-Glu(OMe)-OH into peptides, researchers can delve into the binding affinity and inhibitory potential of these compounds against target enzymes. Such studies yield valuable insights into enzyme mechanisms, playing a pivotal role in the design of potent enzyme inhibitors.

Bioconjugation Strategies: The Boc protecting group present in Boc-DL-Glu(OMe)-OH facilitates sophisticated bioconjugation techniques aimed at attaching biomolecules to diverse surfaces or compounds, enhancing their functionality in biosensors and diagnostic assays. By strategically removing the Boc group post-derivatization, researchers can precisely immobilize or conjugate functionalized peptides or proteins onto desired platforms. This capability drives the advancement of cutting-edge biotechnological applications, including targeted drug delivery systems and diagnostic tools.

1. Quantifying Through-Space Substituent Effects

Rebecca J Burns, Ioulia K Mati, Kamila B Muchowska, Catherine Adam, Scott L Cockroft Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16717-16724. doi: 10.1002/anie.202006943. Epub 2020 Jul 17.

The description of substituents as electron donating or withdrawing leads to a perceived dominance of through-bond influences. The situation is compounded by the challenge of separating through-bond and through-space contributions. Here, we probe the experimental significance of through-space substituent effects in molecular interactions and reaction kinetics. Conformational equilibrium constants were transposed onto the Hammett substituent constant scale revealing dominant through-space substituent effects that cannot be described in classic terms. For example, NO2 groups positioned over a biaryl bond exhibited similar influences as resonant electron donors. Meanwhile, the electro-enhancing influence of OMe/OH groups could be switched off or inverted by conformational twisting. 267 conformational equilibrium constants measured across eleven solvents were found to be better predictors of reaction kinetics than calculated electrostatic potentials, suggesting utility in other contexts and for benchmarking theoretical solvation models.

2. Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation

Barbora Lemrová, Michal Maloň, Miroslav Soural Org Biomol Chem. 2022 May 11;20(18):3811-3816. doi: 10.1039/d2ob00536k.

Immobilized L-aspartic acid beta-methyl ester (Fmoc-Asp(OMe)-OH) was reacted with 4-nitrobenzenesulfonyl chloride, followed by alkylation with various α-haloketones. The resulting intermediates were treated with potassium trimethylsilanolate, which yielded tetrasubstituted pyrroles after a one-step transformation consisting of sequential C-arylation, aldol condensation and spontaneous aromatization. The discovered synthetic strategy enables fast and simple access to pentasubstituted and functionalized pyrroles from a number of readily available starting materials.

3. Covalent Organic Frameworks Doped with Different Ratios of OMe/OH as Fluorescent and Colorimetric Sensors

Jilu Yang, Yuping Cao, Wenbo Si, Jin Zhang, Jiemin Wang, Yi Qu, Wenwu Qin ChemSusChem. 2022 Jun 8;15(11):e202200100. doi: 10.1002/cssc.202200100. Epub 2022 Apr 29.

Improving the luminescence properties of covalent organic frameworks (COFs) has always been an important issue. Here, a series of COFs (([OMe]x -TzDa (TzDa is composed only by monomerics Tz and Da, OMe represents the incorporation of monomeric Dm)) with different ratios of OMe and OH were designed and synthesized. The photochemical behavior of [OMe]x -TzDa changed significantly due to the synergistic effect of aggregation induced emission (AIE), intramolecular charge transfer (ICT), and excited-state intramolecular proton transfer (ESIPT) effects. [OMe]2 -TzDa, which contained a ratio of 2/1 of OMe/OH, showed the strongest fluorescence emission in water and the best linear relationship for the detection of pH. Furthermore, [OMe]2 -TzDa was used to monitor HCl and NH3 gases and showed a color change, visible to the naked eye. Therefore, a "confidential pigment" was successfully made. Moreover, [OMe]2 -TzDa was also applied to detect N2 H4 . The work indicates the [OMe]2 -TzDa can serve as the first fluorescence sensor to detect pH, HCl and NH3 gases, which also shows a good response to N2 H4 .