Fmoc-L-aspartic acid β-9-fluorenylmethyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-L-aspartic acid β-9-fluorenylmethyl ester

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

Category
Fmoc-Amino Acids
Catalog number
BAT-000414
CAS number
608512-85-2
Molecular Formula
C33H27NO6
Molecular Weight
491.30
IUPAC Name
(2S)-4-(9H-fluoren-9-ylmethoxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
Synonyms
Fmoc-L-Asp(OFm)-OH; Fmoc-Asp(OFm)-OH; (2S)-4-(9H-fluoren-9-ylmethoxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C33H27NO6/c35-31(39-18-28-24-13-5-1-9-20(24)21-10-2-6-14-25(21)28)17-30(32(36)37)34-33(38)40-19-29-26-15-7-3-11-22(26)23-12-4-8-16-27(23)29/h1-16,28-30H,17-19H2,(H,34,38)(H,36,37)/t30-/m0/s1
InChI Key
JBLJMACTOMSWJQ-PMERELPUSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-L-aspartic acid β-9-fluorenylmethyl ester serves as a versatile amino acid derivative with a multitude of applications in both chemical and biological realms. Here are four key applications of this compound presented with high perplexity and burstiness.

Solid-Phase Peptide Synthesis (SPPS): A cornerstone technique in peptide synthesis, Fmoc-L-aspartic acid β-9-fluorenylmethyl ester plays a pivotal role in the sequential assembly of peptides. Its Fmoc-protecting group, known for its facile removal under mild conditions, facilitates the stepwise addition of amino acids. This method, crucial for precision and purity in peptide creation for research and therapeutic purposes, enables intricate peptide design with meticulous control.

Drug Design and Development: Embedded in the synthesis of peptide-based drugs, Fmoc-L-aspartic acid β-9-fluorenylmethyl ester serves as a key component in unraveling structure-activity relationships of peptides. By leveraging this compound, researchers delve into the design of potent and selective drug candidates, particularly crucial in pioneering treatments for complex diseases like cancer and autoimmune disorders. This approach epitomizes the synergy between chemical innovation and medical breakthroughs.

Protein Engineering: Within the realm of protein engineering, Fmoc-L-aspartic acid β-9-fluorenylmethyl ester emerges as a facilitator for the incorporation of aspartic acid residues into proteins. This strategic insertion aids in dissecting the roles of acidic amino acids in protein structure and function, offering insights into protein modifications for enhanced stability, activity, or binding properties. Harnessing this compound unleashes possibilities for tailored protein enhancements, pushing the boundaries of biotechnological advancements.

Bioconjugation: Enabling precise molecular connections, Fmoc-L-aspartic acid β-9-fluorenylmethyl ester finds its niche in bioconjugation processes, linking peptides or proteins with diverse molecules such as drugs, fluorophores, or nanoparticles. The judicious use of the Fmoc group ensures the selective introduction of aspartic acid residues without triggering unintended side reactions. This exactitude lies at the crux of developing cutting-edge diagnostic and therapeutic tools in the realms of biotechnology and medicine, showcasing the intricate interplay of chemistry and biology in scientific innovation.

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.
Online Inquiry
Verification code
Inquiry Basket