Need Assistance?

US & Canada:
+
UK: +

FAQs

Resources

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Application Area

Fmoc-L-glutamic acid γ-9-fluorenylmethyl ester

Name: Fmoc-L-glutamic acid γ-9-fluorenylmethyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

* 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-000417

CAS number

608512-86-3

Molecular Formula

C34H29NO6

Molecular Weight

547.60

IUPAC Name

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

Synonyms

Fmoc-L-Glu(OFm)-OH; Fmoc-L-glutamic acid 5-(9-fluorenylmethyl) ester; (2S)-5-(9H-fluoren-9-ylmethoxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid

Appearance

White powder

Purity

≥ 98% (HPLC)

Storage

Store at 2-8 °C

InChI

InChI=1S/C34H29NO6/c36-32(40-19-29-25-13-5-1-9-21(25)22-10-2-6-14-26(22)29)18-17-31(33(37)38)35-34(39)41-20-30-27-15-7-3-11-23(27)24-12-4-8-16-28(24)30/h1-16,29-31H,17-20H2,(H,35,39)(H,37,38)/t31-/m0/s1

InChI Key

VIHCOXHFLJLQJT-HKBQPEDESA-N

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)CCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-L-glutamic acid γ-9-fluorenylmethyl ester (Fmoc-Glu-OH) serves as a key derivative in peptide synthesis, offering a myriad of applications.

Peptide Synthesis: Integral to solid-phase peptide synthesis (SPPS), Fmoc-Glu-OH features a stable and removable Fmoc protective group, allowing for the meticulous construction of peptides in a controlled manner. The facile cleavage of the Fmoc group under mild basic conditions facilitates the incremental addition of amino acids, enabling precise peptide assembly.

Bioconjugation Studies: Within the realm of bioconjugation, Fmoc-Glu-OH emerges as a versatile tool for introducing glutamic acid residues into peptides and proteins, offering functional handles for subsequent chemical modifications. This capability is particularly valuable in crafting peptide conjugates for drug delivery systems and delving into biomolecular interaction studies, unlocking new possibilities for tailored bioapplications.

Protein Engineering: By leveraging Fmoc-Glu-OH in protein engineering endeavors, researchers can synthesize modified proteins endowed with specific functional characteristics. Through strategic incorporation of glutamic acid at targeted sites, protein charge, structure, and solubility can be manipulated, broadening the horizons for custom biocatalysts and therapeutic proteins.

Structural Biology: In the domain of structural biology, derivatives of Fmoc-Glu-OH prove indispensable for probing protein structure and function. Through integration of these derivatives into peptides, scientists can explore the role of glutamic acid in protein folding and stability, shedding light on intricate protein dynamics and interactions at a molecular level, advancing our comprehension of the complex world of proteins.

1. 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.

2. 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.

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.