Fmoc-N-amido-PEG1-acetic acid

Name: Fmoc-N-amido-PEG1-acetic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 260367-12-2

Cat No.: BP-500167

Purity: ≥95% 4.5

Fmoc-N-amido-PEG1-acetic acid is an Fmoc-protected, PEG-based carboxylic acid building block designed for constructing PROTAC linkers and other targeted-degradation conjugates. Structurally, it combines an N-amide functionality with a short polyethylene glycol segment terminated by an acetic acid group, while the fluorenylmethoxycarbonyl (Fmoc) group provides orthogonal protection for controlled stepwise synthesis. In PROTAC architectures, such PEG–amide linkers are used to tune the spatial relationship between the ligand-binding warhead and the recruiting/effector module, improving productive ternary complex formation by increasing conformational flexibility and reducing steric clashes. The terminal carboxyl group enables amide coupling to partner fragments, facilitating modular assembly of degraders. As a compact PEG linker, it is valuable for optimizing linker length, polarity, and solubility in iterative structure–activity studies, supporting reliable synthesis of degraders for biochemical and cell-based evaluation.

Structure of 260367-12-2

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Category

PROTAC Linker

Molecular Formula

C19H19NO5

Molecular Weight

341.36

Related CAS

675606-79-8 (polymer)

Appearance

Pale Yellow or Colorless Oily Matter

* For research and manufacturing use only. Not for human or clinical use.

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Popular Publications Citing BOC Sciences Products

Purity

≥95%

Solubility

Soluble in DMSO (10 mm)

Appearance

Pale Yellow or Colorless Oily Matter

Application

2-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic Acid can be used as reactant/reagent in modular platform to develop peptoid-based selective fluorescent metal sensors.

Storage

Store at -20°C, keep in dry and avoid sunlight

Shipping

Room temperature

IUPACName

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

Synonyms

Fmoc-NH-PEG1-CH2COOH; Fmoc-O1Pen-OH; 5- (Fmoc- amino) - 3- oxapentanoic Acid; 5-(9-Fluorenylmethyloxycarbonyl-amino)-3-oxapentanoic acid; Acetic acid, 2-[2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethoxy]-; Fmoc-AEA-OH; 2-[2-(Fmoc-amino)ethoxy]acetic Acid

Boiling Point

602.6±40.0°C (Predicted)

Melting Point

83-89°C

Density

1.287±0.06 g/cm3 (Predicted)

InChI Key

LBVXPUINIMIGAU-UHFFFAOYSA-N

InChI

InChI=1S/C19H19NO5/c21-18(22)12-24-10-9-20-19(23)25-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,17H,9-12H2,(H,20,23)(H,21,22)

SMILES

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

Biological Activity

Fmoc-NH-PEG1-CH2COOH is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[1] . In Vitro: ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker

1. 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.

2. 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.

3. 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.

Fmoc-N-amido-PEG1-acetic acid is a polyethylene glycol-based linker building block designed for assembling PROTAC constructs where controlled spacing and solubility can be advantageous for ternary-complex formation. Its Fmoc-protected amide functionality enables stepwise synthesis, while the PEG segment supports aqueous compatibility and flexible linker behavior. The following sections describe its structural features and practical reactivity considerations for linker incorporation into targeted protein degradation molecules.

Structure: The linker contains an Fmoc-protected amide at one terminus and an acetic acid functionality at the other, connected through a short PEG-derived segment. It features aromatic carbamate/amide linkages, ether-containing PEG units, and hydrogen-bonding-capable groups that influence solubility and conformational flexibility.

Reactivity: This building block is typically incorporated via amide-forming coupling reactions using standard peptide-coupling chemistries under anhydrous conditions, with base to promote activation and nucleophilic attack. The Fmoc group is removed under mild base conditions to reveal the reactive amine for subsequent coupling steps. Solvents such as polar aprotic media are commonly used to ensure adequate solvation and efficient coupling, while maintaining compatibility with PROTAC synthesis workflows.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂