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Application Area

Boc-L-aspartic acid α-9-fluorenylmethyl ester

* 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-004527

CAS number

129046-87-3

Molecular Formula

C23H25NO6

Molecular Weight

411.46

Boc-L-aspartic acid α-9-fluorenylmethyl ester

IUPAC Name

(3S)-4-(9H-fluoren-9-ylmethoxy)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid

Synonyms

Boc-L-Asp-Ofm; (S)-4-((9H-Fluoren-9-yl)methoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Appearance

White powder

Purity

≥ 99% (TLC)

Density

1.251 g/cm3

Melting Point

138-142°C

Storage

Store at 2-8 °C

InChI

InChI=1S/C23H25NO6/c1-23(2,3)30-22(28)24-19(12-20(25)26)21(27)29-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,24,28)(H,25,26)/t19-/m0/s1

InChI Key

RMRKPGGMJKNMSK-IBGZPJMESA-N

Canonical SMILES

CC(C)(C)OC(=O)NC(CC(=O)O)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Boc-L-aspartic acid α-9-fluorenylmethyl ester, a versatile chemical compound with widespread applications in synthetic organic chemistry and biochemistry, is at the forefront of scientific innovation. Here are four key applications:

Peptide Synthesis: Central to solid-phase peptide synthesis (SPPS), Boc-L-aspartic acid α-9-fluorenylmethyl ester plays a pivotal role in crafting intricate peptides. This compound acts as a shielded amino acid, ensuring the seamless integration of the aspartic acid residue into the burgeoning peptide chain. Such protection is paramount in thwarting unwanted side reactions, culminating in the production of high-yield, high-purity peptides instrumental for both research endeavors and therapeutic interventions.

Protein Labeling: Delving into protein labeling methodologies, the α-9-fluorenylmethyl ester group emerges as a potent tool for selectively tagging proteins. This compound empowers the fluorescent labeling of proteins, streamlining their visualization and monitoring in diverse biochemical assays and imaging studies. These labeling strategies are indispensable for unraveling the intricate dynamics, interactions, and localization patterns of proteins within the cellular milieu.

Drug Development: In the realm of medicinal chemistry, Boc-L-aspartic acid α-9-fluorenylmethyl ester shines as a cornerstone in synthesizing peptide-based drug candidates with immense therapeutic potential. Serving as a versatile building block, this compound seamlessly integrates into pharmaceutical formulations, fine-tuning their biological activity. This strategic approach fuels the discovery and development of novel therapeutics targeting a spectrum of ailments, encompassing cancer and metabolic disorders.

Bioconjugation: Navigating the realm of bioconjugation, Boc-L-aspartic acid α-9-fluorenylmethyl ester assumes a crucial role as a versatile linker or spacer in intricate biochemical reactions. This compound facilitates the fusion of bioactive molecules such as peptides or drugs with other biomolecules or surfaces, spawning tailored delivery systems, diagnostic probes, and biomaterials imbued with augmented functionality. This dynamic capability underpins the creation of innovative platforms, driving advancements in various biomedical applications.

1. Photocatalytic direct borylation of carboxylic acids

Qiang Wei, Yuhsuan Lee, Weiqiu Liang, Xiaolei Chen, Bo-Shuai Mu, Xi-Yang Cui, Wangsuo Wu, Shuming Bai, Zhibo Liu Nat Commun. 2022 Nov 19;13(1):7112. doi: 10.1038/s41467-022-34833-1.

The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.

2. Tris(pentafluorophenyl)borane-Catalyzed Reactions Using Silanes

Taylor Hackel, Nicholas A McGrath Molecules. 2019 Jan 25;24(3):432. doi: 10.3390/molecules24030432.

The utility of an electron-deficient, air stable, and commercially available Lewis acid tris(pentafluorophenyl)borane has recently been comprehensively explored. While being as reactive as its distant cousin boron trichloride, it has been shown to be much more stable and capable of catalyzing a variety of powerful transformations, even in the presence of water. The focus of this review will be to highlight those catalytic reactions that utilize a silane as a stoichiometric reductant in conjunction with tris(pentafluorophenyl) borane in the reduction of alcohols, carbonyls, or carbonyl-like derivatives.

3. Boronate-Based Fluorescent Probes as a Prominent Tool for H2O2 Sensing and Recognition

Ling Wang, Xuben Hou, Hao Fang, Xinying Yang Curr Med Chem. 2022;29(14):2476-2489. doi: 10.2174/0929867328666210902101642.

Given the crucial association of hydrogen peroxide with a wide range of human diseases, this compound has currently earned the reputation of being a popular biomolecular target. Although various analytical methods have attracted our attention, fluorescent probes have been used as prominent tools to determine H2O2 to reflect the physiological and pathological conditions of biological systems. The sensitive responsive part of these probes is the boronate ester and boronic acid groups, which are important reporters for H2O2 recognition. In this review, we summarize boronate ester/boronic acid group-based fluorescent probes for H2O2 reported from 2012 to 2020, and we have generally classified the fluorophores into six categories to exhaustively elaborate the design strategy and comprehensive systematic performance. We hope that this review will inspire the exploration of new fluorescent probes based on boronate ester/boronic acid groups for the detection of H2O2 and other relevant analytes.