Name: Fmoc-N-amido-PEG5-acetic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Fmoc-NH-PEG5-CH2COOH; Fmoc-NH-5(ethylene glycol)-acetic acid; Fmoc-PEG5-acetic acid; 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azahenicosan-21-oic acid; 17-[(9-Fluorenylmethoxycarbonyl)amino]-3,6,9,12,15-pentaoxaheptadecanoic acid; 5,8,11,14,17-Pentaoxa-2-azanonadecanedioic acid 1-(9H-fluoren-9-ylmethyl) ester; 2,7,10,13,16,19-Hexaoxa-4-azaheneicosan-21-oic acid, 1-(9H-fluoren-9-yl)-3-oxo-

IUPAC Name

2-[2-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCOCCOCCOCCOCCOCC(=O)O

InChI

InChI=1S/C27H35NO9/c29-26(30)20-36-18-17-35-16-15-34-14-13-33-12-11-32-10-9-28-27(31)37-19-25-23-7-3-1-5-21(23)22-6-2-4-8-24(22)25/h1-8,25H,9-20H2,(H,28,31)(H,29,30)

InChIKey

LNIFRTLAPAPKAG-UHFFFAOYSA-N

Density

1.224±0.06 g/cm3 (Predicted)

Solubility

Soluble in DMSO (10 mm)

PSA

121.78000

Appearance

Pale Yellow or Colorless Oily Liquid

Shipping

Room temperature

Storage

Store at 2-8°C

Boiling Point

704.3±60.0°C (Predicted)

Fmoc-N-amido-PEG5-acetic acid is a versatile compound widely used in peptide and bioconjugation chemistry. The Fmoc (9-fluorenylmethyloxycarbonyl) group protects the amino terminus, facilitating stepwise synthesis of peptides in solid-phase peptide synthesis (SPPS). This protection ensures controlled addition of amino acid residues and other functional moieties, making it a critical building block in the development of functionalized peptides and complex biomolecules.

A key feature of Fmoc-N-amido-PEG5-acetic acid is the incorporation of a polyethylene glycol (PEG) chain with five ethylene glycol units. The PEG5 moiety enhances the solubility and flexibility of the compound, which is particularly advantageous in bioconjugation. The PEG chain acts as a hydrophilic spacer, reducing steric hindrance and improving the bioavailability, stability, and pharmacokinetics of peptide-based drugs or conjugates. This functionality makes the compound essential for the synthesis of biocompatible and long-circulating therapeutic agents.

Fmoc-N-amido-PEG5-acetic acid is extensively used in the development of peptide-drug conjugates (PDCs) and antibody-drug conjugates (ADCs). The PEG5 spacer facilitates the precise attachment of cytotoxic agents, targeting ligands, or imaging probes to peptides or antibodies while maintaining their bioactivity. This tailored conjugation improves drug targeting to diseased tissues, such as tumors, while minimizing off-target effects, making it crucial for advanced drug delivery systems.

Another significant application of Fmoc-N-amido-PEG5-acetic acid is in the design of self-assembling peptides and hydrogels. The PEG chain enhances the hydrophilic properties of peptides, promoting the formation of stable nanostructures such as micelles, vesicles, or hydrogels. These structures have broad applications in drug delivery, regenerative medicine, and tissue engineering. The flexibility of the PEG5 linker allows researchers to fine-tune the physical and chemical properties of the resulting materials, optimizing their performance for specific biomedical applications.

Additionally, Fmoc-N-amido-PEG5-acetic acid is used in surface modification and biomaterials engineering. It enables the attachment of peptides or other bioactive molecules to surfaces, such as nanoparticles, hydrogels, or biosensors, to improve biocompatibility and functionalization. This capability is highly valuable in creating targeted delivery systems, diagnostic tools, and biosensing devices, ensuring precise interactions with biological environments.

1. Acidity characterization of heterogeneous catalysts by solid-state NMR spectroscopy using probe molecules

Anmin Zheng, Shang-Bin Liu, Feng Deng Solid State Nucl Magn Reson. 2013 Oct-Nov;55-56:12-27. doi: 10.1016/j.ssnmr.2013.09.001. Epub 2013 Sep 20.

Characterization of the surface acidic properties of solid acid catalysts is a key issue in heterogeneous catalysis. Important acid features of solid acids, such as their type (Brønsted vs. Lewis acid), distribution and accessibility (internal vs. external sites), concentration (amount), and strength of acid sites are crucial factors dictating their reactivity and selectivity. This short review provides information on different solid-state NMR techniques used for acidity characterization of solid acid catalysts. In particular, different approaches using probe molecules containing a specific nucleus of interest, such as pyridine-d5, 2-(13)C-acetone, trimethylphosphine, and trimethylphosphine oxide, are compared. Incorporation of valuable information (such as the adsorption structure, deprotonation energy, and NMR parameters) from density functional theory (DFT) calculations can yield explicit correlations between the chemical shift of adsorbed probe molecules and the intrinsic acid strength of solid acids. Methods that combine experimental NMR data with DFT calculations can therefore provide both qualitative and quantitative information on acid sites.

2. The Stephan Curve revisited

William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.

The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.

3. Atroposelective Synthesis of 1,1'-Bipyrroles Bearing a Chiral N-N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence

Yaru Gao, Luo-Yu Wang, Tao Zhang, Bin-Miao Yang, Yu Zhao Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202200371. doi: 10.1002/anie.202200371. Epub 2022 Feb 24.

We present herein a highly efficient atroposelective synthesis of axially chiral 1,1'-bipyrroles bearing an N-N linkage from simple hydrazine and 1,4-diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)-catalyzed double Paal-Knorr reaction, an intriguing Fe(OTf)3 -induced enantiodivergence was also observed.

Catalog	Product Name	CAS
BADC-00982	Fmoc-N-amido-PEG2-acetic acid	166108-71-0
BADC-01112	Fmoc-N-amido-PEG1-acetic acid	260367-12-2
BADC-01124	Fmoc-N-amido-PEG4-acetic acid	437655-95-3
BADC-01954	Fmoc-N-amido-PEG6-acetic acid	437655-96-4
BADC-01175	Fmoc-N-amido-PEG8-acetic acid	868594-52-9

Why is Fmoc-N-amido-PEG5-acetic acid used in ADC synthesis?

Fmoc-N-amido-PEG5-acetic acid is a protected linker used to introduce PEG5 spacers in ADCs. The Fmoc group protects the amine during conjugation, allowing selective deprotection for controlled payload attachment while enhancing solubility and reducing steric constraints.

15/12/2019

Dear BOC Sciences, how is the Fmoc group removed from Fmoc-N-amido-PEG5-acetic acid?

The Fmoc protecting group can be removed under standard base treatment, such as piperidine in DMF, exposing the primary amine for subsequent conjugation to cytotoxic payloads or other functional groups in ADC synthesis.

5/10/2017

Dear BOC Sciences, what advantages does the PEG5 spacer provide?

The PEG5 spacer in Fmoc-N-amido-PEG5-acetic acid improves solubility, reduces aggregation, and provides flexibility between the antibody and payload, enhancing ADC stability and minimizing steric hindrance during target engagement.

30/9/2019

Dear team, which analytical techniques confirm Fmoc-N-amido-PEG5-acetic acid integrity?

HPLC is used to assess purity, mass spectrometry confirms molecular weight, and NMR spectroscopy verifies the Fmoc protection and PEG5 structure, ensuring reliability for ADC development workflows.

2/2/2021

Dear team, what are the recommended handling precautions for Fmoc-N-amido-PEG5-acetic acid?

Fmoc-N-amido-PEG5-acetic acid should be handled with gloves and protective equipment, stored in a cool, dry environment protected from light and moisture. Inert gas or vacuum storage is advised to maintain chemical stability. Supporting documentation includes detailed handling instructions.

26/12/2018

— Dr. Oliver Brown, Senior Scientist (UK)

Fmoc-N-amido-PEG5-acetic acid delivered smooth peptide coupling with high efficiency.

30/9/2019

— Ms. Clara Weber, Biochemist (Germany)

Excellent lot quality enabled consistent multi-step linker synthesis.

26/12/2018

— Dr. Ethan Parker, Medicinal Chemist (USA)

Fmoc protection remained stable throughout the synthesis process.

2/2/2021

— Dr. Sophie Moreau, Senior Scientist (France)

The reagent simplified purification and minimized side reactions.

15/12/2019

— Dr. Liam Fischer, Chemist (UK)

Using this product, we developed new linker architectures for improved ADC performance.

— Dr. Sophia Lee, Peptide Chemist (Germany)

Fmoc-N-amido-PEG5-acetic acid allowed smooth solid-phase synthesis in our peptide modification projects. BOC Sciences provided rapid support when needed.

5/10/2017