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

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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

IUPAC Name

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

SMILES

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

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)

InChIKey

LBVXPUINIMIGAU-UHFFFAOYSA-N

Density

1.287±0.06 g/cm3 (Predicted)

Solubility

Soluble in DMSO (10 mm)

Melting Point

83-89°C

Flash Point

294.8±30.1 °C

Index Of Refraction

1.630

PSA

84.86000

Vapor Pressure

0.0±1.6 mmHg at 25°C

Appearance

Pale Yellow or Colorless Oily Matter

Shipping

Room temperature

Storage

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

Boiling Point

602.6±40.0°C (Predicted)

Form

Solid

Related CAS

675606-79-8 (polymer)

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

Fmoc-N-amido-PEG1-acetic acid, a versatile chemical linker, finds wide utilization in biochemical and pharmaceutical research. Below are four key applications of this compound:

Peptide Synthesis: Integral to solid-phase peptide synthesis, Fmoc-N-amido-PEG1-acetic acid plays a crucial role in constructing peptides. The Fmoc group shields the terminal amino group throughout the synthesis process, enabling the sequential addition of amino acids. This method offers researchers a dependable approach to creating intricate peptides with elevated yields and purity levels.

Drug Delivery: This compound serves as a cornerstone in designing drug delivery systems that leverage PEG to enhance drug solubility, stability, and biocompatibility. By conjugating drugs to Fmoc-N-amido-PEG1-acetic acid, researchers can enhance the pharmacokinetic properties of the resulting compounds. This augmentation not only boosts therapeutic efficacy but also mitigates the adverse effects associated with drug treatments.

Surface Modification: Employing Fmoc-N-amido-PEG1-acetic acid enhances the biocompatibility and functionality of nanoparticle surfaces, biomaterials, and medical devices. The PEG component forms a hydrophilic layer that reduces protein adsorption and cellular interactions, crucial for applications spanning biosensors to implantable devices. This modification guarantees the stability and optimal performance of these devices within biological settings.

Protein Engineering: In the realm of protein engineering, Fmoc-N-amido-PEG1-acetic acid enables site-specific PEGylation of proteins, enhancing their pharmacokinetic characteristics. By attaching PEG chains to precise residues, researchers can prolong the circulation time of therapeutic proteins in the bloodstream while lowering their immunogenicity. This transformation renders the proteins more suitable for diverse therapeutic applications, promising advancements in the realm of medical treatments.

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.

Catalog	Product Name	CAS
BADC-00982	Fmoc-N-amido-PEG2-acetic acid	166108-71-0
BADC-01124	Fmoc-N-amido-PEG4-acetic acid	437655-95-3
BADC-01954	Fmoc-N-amido-PEG6-acetic acid	437655-96-4
BADC-01142	Fmoc-N-amido-PEG5-acetic acid	635287-26-2
BADC-01175	Fmoc-N-amido-PEG8-acetic acid	868594-52-9