Fmoc-L-aspartic acid β-2-phenylisopropyl ester
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Fmoc-L-aspartic acid β-2-phenylisopropyl ester

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An aspartic acid derivative allowing specific side chain deprotection with 1% TFA in dichloromethane.

Category
Fmoc-Amino Acids
Catalog number
BAT-003741
CAS number
200336-86-3
Molecular Formula
C28H27NO6
Molecular Weight
473.53
Fmoc-L-aspartic acid β-2-phenylisopropyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-(2-phenylpropan-2-yloxy)butanoic acid
Synonyms
Fmoc-L-Asp(2-phenylisopropyloxy)-OH; FMOC-ASP(2-PHENYLISOPROPYL ESTER)-OH; FMOC-ASP(OPIS)-OH; FMOC-ASP[BZL(ME2)]-OH; FMOC-ASPARTIC ACID(2-PHENYLISOPROPYL ESTER)
Appearance
White to off-white powder
Purity
≥ 99% (HPLC, Chiral purity)
Density
1.266±0.06 g/cm3
Boiling Point
687.3±55.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C28H27NO6/c1-28(2,18-10-4-3-5-11-18)35-25(30)16-24(26(31)32)29-27(33)34-17-23-21-14-8-6-12-19(21)20-13-7-9-15-22(20)23/h3-15,23-24H,16-17H2,1-2H3,(H,29,33)(H,31,32)/t24-/m0/s1
InChI Key
MEAHCBOPNIDLFH-DEOSSOPVSA-N
Canonical SMILES
CC(C)(C1=CC=CC=C1)OC(=O)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-aspartic acid β-2-phenylisopropyl ester plays a pivotal role in peptide synthesis and various bioscience applications. Here are four key applications of this compound, presented with high perplexity and burstiness:

Solid-Phase Peptide Synthesis: Essential for solid-phase peptide synthesis (SPPS), Fmoc-L-aspartic acid β-2-phenylisopropyl ester is a linchpin in crafting intricate peptides of utmost purity. It facilitates the integration of aspartic acid residues while preserving their side-chain integrity—a critical step in generating bioactive peptides with meticulously defined sequences for both research and therapeutic ventures.

Proteomics Research: Within the realm of proteomics, this compound serves as a cornerstone for unraveling the complexities of protein structure and function. By enabling the synthesis of peptides that mimic protein fragments, it aids researchers in utilizing these peptides as benchmarks in mass spectrometry analyses to identify and quantify proteins within intricate samples. This compound is instrumental in shedding light on protein-protein interactions and post-translational modifications, enriching our understanding of cellular processes.

Drug Development: Valued in the realm of drug development, Fmoc-L-aspartic acid β-2-phenylisopropyl ester plays a critical role in optimizing peptide-based drug candidates. By incorporating derivatives of aspartic acid into therapeutic agents, scientists can fine-tune pharmacokinetic properties and bolster drug stability. This approach facilitates the design of potent therapeutic peptides tailored to exhibit targeted biological activities, thereby advancing the field of drug discovery.

Bioconjugation Techniques: Embraced in bioconjugation methodologies, this compound serves as a linchpin in tethering peptides to diverse molecules like fluorophores or drugs for various diagnostic and therapeutic applications. It empowers the site-specific attachment of functional groups to peptides without disturbing their inherent structure—a fundamental aspect in constructing conjugates for diagnostic assays and precision-targeted drug delivery systems, driving innovation in biomedical research.

1. 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.
2. 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.
3. 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.
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