Fmoc-D-aspartic acid β-methylpentyl ester
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Fmoc-D-aspartic acid β-methylpentyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-001992
CAS number
1926162-97-1
Molecular Formula
C25H29NO6
Molecular Weight
439.51
IUPAC Name
2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(3-methylpentan-3-yloxy)-4-oxobutanoic acid
Synonyms
Fmoc-D-Asp(OMpe)-OH; D-Aspartic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 4-(1-ethyl-1-methylpropyl) ester
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.2±0.1 g/cm3
Melting Point
100-106°C
Boiling Point
635.9±55.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H29NO6/c1-4-25(3,5-2)32-22(27)14-21(23(28)29)26-24(30)31-15-20-18-12-8-6-10-16(18)17-11-7-9-13-19(17)20/h6-13,20-21H,4-5,14-15H2,1-3H3,(H,26,30)(H,28,29)
InChI Key
SYGKUYKLHYQKPL-UHFFFAOYSA-N
Canonical SMILES
CCC(C)(CC)OC(=O)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-aspartic acid β-methylpentyl ester, a derivative of aspartic acid utilized in peptide synthesis and research, boasts diverse applications. Here are four key applications:

Peptide Synthesis: Serving as a staple in solid-phase peptide synthesis, Fmoc-D-aspartic acid β-methylpentyl ester plays a pivotal role. Its protected amino group ensures seamless integration into burgeoning peptide chains, mitigating unwanted side reactions. This process facilitates the assembly of intricate peptides tailored for both research endeavors and therapeutic interventions.

Protein Engineering: Within the realm of protein engineering, Fmoc-D-aspartic acid β-methylpentyl ester emerges as a key player in introducing D-amino acids into proteins. This strategic maneuver can enhance protein stability, function, and resistance to proteolytic degradation. Such modifications are essential for crafting more potent therapeutic proteins and peptide-based medications, advancing the frontier of biopharmaceutical innovation.

Biomedical Research: Delving into protein-protein interactions and biomolecular recognition, Fmoc-D-aspartic acid β-methylpentyl ester serves as a valuable tool. By incorporating this ester into peptides and proteins, researchers can unravel how specific residues influence binding affinity and specificity. This profound understanding underpins drug discovery efforts and bolsters the development of cutting-edge diagnostic technologies, fostering breakthroughs in biomedical research.

Material Science: Beyond its conventional biochemical applications, the exceptional properties of Fmoc-D-aspartic acid β-methylpentyl ester find utility in the realm of material science. By harnessing its unique characteristics, peptide-based materials can be tailored for diverse applications like tissue engineering, drug delivery systems, and the fabrication of biomimetic surfaces. This versatility underscores the compound’s significance in shaping innovative solutions across varied scientific domains.

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. 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. 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.
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