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Application Area

Fmoc-L-glutamic acid γ-cyclohexyl 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-003758

CAS number

150047-85-1

Molecular Formula

C26H29NO6

Molecular Weight

451.50

IUPAC Name

(2S)-5-cyclohexyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid

Synonyms

Fmoc-L-Glu(OcHex)-OH; Fmoc-L-glutamic acid 5-cyclohexyl ester; (2S)-5-cyclohexyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid

Appearance

White powder

Purity

≥ 98% (HPLC)

Melting Point

84-87 °C

Storage

Store at 2-8 °C

InChI

InChI=1S/C26H29NO6/c28-24(33-17-8-2-1-3-9-17)15-14-23(25(29)30)27-26(31)32-16-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h4-7,10-13,17,22-23H,1-3,8-9,14-16H2,(H,27,31)(H,29,30)/t23-/m0/s1

InChI Key

ODIPEUXZAYGDMU-QHCPKHFHSA-N

Canonical SMILES

C1CCC(CC1)OC(=O)CCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-glutamic acid γ-cyclohexyl ester, a synthetic compound crucial in peptide synthesis and research, finds diverse applications.

Peptide Synthesis: A cornerstone in solid-phase peptide synthesis, Fmoc-L-glutamic acid γ-cyclohexyl ester serves as a protected building block, ensuring stability for the carboxyl group and enabling selective deprotection during peptide chain elongation. This intricate process facilitates the meticulous assembly of complex peptides and proteins with tailored sequences.

Drug Development: By incorporating Fmoc-L-glutamic acid γ-cyclohexyl ester, researchers can manipulate properties like solubility, stability, and bioavailability in medicinal peptides. This strategic approach fosters the creation of peptide drugs with optimized pharmacological profiles, driving innovation in drug development.

Bioconjugation Studies: Within the realm of biochemistry, the versatility of Fmoc-L-glutamic acid γ-cyclohexyl ester allows for its integration into bioconjugation experiments, facilitating the linkage of peptides to other biomolecules. This adaptability is particularly valuable in crafting peptide conjugates for targeted drug delivery or investigating biological interactions in intricate systems.

Proteomics Research: In the landscape of proteomics, Fmoc-L-glutamic acid γ-cyclohexyl ester is harnessed to synthesize labeled peptides for mass spectrometry analysis. These labeled peptides serve as standards or markers in quantitative proteomics, enabling precise measurements of protein expression levels. This precision aids in identifying and quantifying proteins, shedding light on cellular pathways and disease-related processes, unveiling the intricacies of proteomics research.

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.

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