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Fmoc-N-amido-dPEG®₃-acid (QBD-10033)

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Description

Fmoc-N-amido-dPEG®3-acid, product number QBD-10033, is one of a broad line of products designed for use in peptide synthesis. The short (13 atoms), discrete PEG (dPEG®) spacer is functionalized with a propionic acid group on one end and Fmoc-protected amine on the other. The product can be added to the N-terminus of a growing peptide chain or to a primary-amine-functionalized side chain of an amino acid such as lysine. The dPEG®3 spacer imparts water solubility to the peptide to which it is conjugated.

QBD-10033 permits our customers to insert a dPEG® spacer into a peptide chain using familiar Fmoc chemistry using solid phase or solution phase chemistry. The dPEG® compound can be inserted at either end of the peptide chain or in the middle of two amino acid sequences to provide a flexible linker between distinct functional peptides. Additionally, the dPEG® spacer can be used to provide spacing in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® products means that the construct gains hydrodynamic volume and water solubility while remaining soluble in organic solvent. The Fmoc protecting group removes easily with a solution of piperidine in N,N-dimethylformamide (DMF).

Specifications

Unit Size 1000 mg
Molecular Weight 443.49; single compound
Chemical formula C₂₄H₂₉NO₇
CAS
867062-95-1
Purity > 98%
Spacers
dPEG® Spacer is 13 atoms and 14.4 Å
Shipping
Ambient
Typical solubility properties (for additional information contact Customer Support) Methylene chloride, Acetontrile, DMAC or DMSO.
Storage and handling -20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

References

  1. Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

  2. Trivalent PEGylated Platform for the Conjugation of Bioactive Compounds. Angela Torres, Carlos Mas-Moruno, Enrique Perez-Paya, Fernando Albericio, and Miriam Royo. Bioconjugate Chem. 2011, 22 (10), pp 2172–2178. August 25, 2011. DOI: 10.1021/bc100393g.

  3. Development of Peptide Nucleic Acid Probes for Detection of the HER2 Oncogene. Belhu Metaferia., Jun S. Wei., Young K. Song, Jennifer Evangelista, Konrad Aschenbach, Peter Johansson, Xinyu Wen, Qingrong Chen, Albert Lee, Heidi Hempel, Jinesh S. Gheeya, Stephanie Getty, Romel Gomez, Javed Khan. PLoS ONE. 2012, 8 (4) e58870. April 10, 2013. DOI: 10.1371/journal.pone.0058870.

  4. Enhanced Cellular Uptake of Peptide-Targeted Nanoparticles through Increased Peptide Hydrophilicity and Optimized Ethylene Glycol Peptide-Linker Length. Jared F. Stefanick, Jonathan D. Ashley, and Basar Bilgicer. ACS Nano. 2013, 7 (9) pp 8115–8127. August 29, 2013. DOI: 10.1021/nn4033954.

  5. Quantifying Cellular Internalization with a Fluorescent Click Sensor. Laura I. Selby, Luigi Aurelio, Daniel Yuen, Bim Graham, and Angus P. R. Johnston. ACS Sensors. 2018, 3, pp 1182-1189. April 20, 2018. DOI: 10.1021/acssensors.8b00219.

  6. Fc-Binding Antibody-Recruiting Molecules Targeting Prostate-Specific Membrane Antigen: Defucosylation of Antibody for Efficacy Improvement. Sasaki K, Harada M, Yoshikawa T, Tagawa H, Harada Y, Yonemitsu Y, Ryujin T, Kishimura A, Mori T, Katayama Y. Preprint from ChemRxiv, 14 Jul 2020
    DOI: 10.26434/chemrxiv.12654602.v1 PPR: PPR187646

  7. Peptide Amphiphilic-Based Supramolecular Structures with Anti-HIV-1 Activity. Gómara Elena, María José, Pons Pons, Ramon; Herrera, Carolina, Ziprin, Paul, Haro Villar, Isabel Haro. Bioconjugate Chemistry. 2021. Volume 32, Issue 9. 07/13/2021. DOI: 10.1021/acs.bioconjchem.1c00292

Applicable patents and legal notices are available at legal notices.

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