Name: Fmoc-N-amido-PEG8-acetic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Fmoc-NH-PEG8-CH2COOH; 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16,19,22,25,28-nonaoxa-4-azatriacontan-30-oic acid; Fmoc-PEG8-acetic acid; 26-[(9-Fluorenylmethoxycarbonyl)amino]-3,6,9,12,15,18,21,24-octaoxahexacosanoic acid; 5,8,11,14,17,20,23,26-Octaoxa-2-azaoctacosanedioic acid 1-(9H-fluoren-9-ylmethyl) ester; Fmoc-NH-8(ethylene glycol)-acetic acid; 2,7,10,13,16,19,22,25,28-Nonaoxa-4-azatriacontan-30-oic acid, 1-(9H-fluoren-9-yl)-3-oxo-

IUPAC Name

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

Canonical SMILES

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

InChI

InChI=1S/C33H47NO12/c35-32(36)26-45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-10-9-34-33(37)46-25-31-29-7-3-1-5-27(29)28-6-2-4-8-30(28)31/h1-8,31H,9-26H2,(H,34,37)(H,35,36)

InChIKey

JRLUSGRARXJCNA-UHFFFAOYSA-N

Density

1.201±0.06 g/cm3 (Predicted)

Solubility

Soluble in DMSO (10 mm)

PSA

149.47000

Appearance

Pale Yellow Oily Matter

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

Room temperature

Storage

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

Boiling Point

773.7±60.0°C (Predicted)

Form

Solid

Fmoc-N-amido-PEG8-acetic acid, a versatile linker prevalent in peptide and protein chemistry, showcases a multitude of applications across various fields. Here are four key applications of this compound:

Peptide Synthesis: Positioned at the heart of solid-phase peptide synthesis (SPPS), Fmoc-N-amido-PEG8-acetic acid stands as a crucial instrument for constructing elaborate and extended peptides. The incorporation of a polyethylene glycol (PEG) spacer not only boosts solubility but also mitigates aggregation, streamlining the synthesis and purification processes. Researchers harness this linker to fabricate peptides tailored for drug development, molecular biology inquiries, and therapeutic endeavors.

Protein Conjugation: Acting as a cornerstone in protein conjugation, this compound facilitates the coupling of proteins with an array of biomolecules spanning from drugs to fluorophores to other peptides. Serving as a flexible and hydrophilic bridge, the linker preserves the biological functionality of proteins while enhancing their solubility and stability. This capability proves pivotal in fabricating bioconjugates for targeted drug delivery systems and diagnostic applications.

Drug Delivery Systems: Standing at the forefront of drug delivery innovation, Fmoc-N-amido-PEG8-acetic acid plays a pivotal role in crafting cutting-edge drug delivery platforms, including nanoparticle and liposome formulations. Through the process of PEGylation, the pharmacokinetic properties are bolstered while reducing the immunogenicity of delivery systems. By affixing this linker to therapeutic agents, researchers can precisely modulate drug release profiles, amplifying treatment efficacy and reinforcing patient adherence.

Surface Functionalization: Within the realm of surface chemistry, this linker emerges as a key protagonist in functionalizing biomaterial surfaces to augment biocompatibility and anti-fouling attributes. PEGylation of surfaces, such as implants or biosensors, diminishes protein adsorption and cell adhesion, thereby enhancing device functionality and durability. This advancement elevates the utility of biotechnological devices in medical and analytical settings, underscoring the significance of surface modification in optimizing device performance and longevity with intricate precision.

1. 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.

2. 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.

3. 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.

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-01142	Fmoc-N-amido-PEG5-acetic acid	635287-26-2