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Fmoc-N-amido-dPEG®₆-acid (QBD-10063)

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Description

Fmoc-N-amido-dPEG®6-acid, product number QBD-10063, is one of a broad line of products designed for use in peptide synthesis. The short (22 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®6 spacer imparts water solubility to the peptide to which it is conjugated.

QBD-10063 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 100 mg, 1000 mg
Molecular Weight 575.65; single compound
Chemical formula C₃₀H₄₁NO₁₀
CAS
882847-34-9
Purity > 98%
Spacers
dPEG® Spacer is 22 atoms and 25.1 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.
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  8. 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.
  9. Novel Monodisperse PEGtide Dendrons: Design, Fabrication, and Evaluation of Mannose Receptor-Mediated Macrophage Targeting. Jieming Gao, Peiming Chen, Yashveer Singh, Xiaoping Zhang, Zoltan Szekely, Stanley Stein, and Patrick J. Sinko. Bioconjugate Chem. 2013, 24 (8) pp 1332–1344. June 29, 2013. DOI: 10.1021/bc400011v.
  10. B-Peptide Conjugates: Syntheses and CD and NMR Investigations of B/a-Chimeric Peptides, of a DPA-B-Decapeptide, and of a PEGylated b-Heptapeptide. James Gardiner, Raveendra I. Mathad, Berhard Jaun, Jurg V. Schreiber, Oliver Flogel, and Dieter Seebach. Helvetica Chimica Acta. 2009, 92 (12) pp 2698-2721. December 17, 2009. DOI: 10.1002/hlca.200900325.
  11. Immunomodulation of the NLRP3 Inflammasome through Structure-Based Activator Design and Functional Regulation via Lysosomal Rupture. Saikat Manna, William J. Howitz, Nathan J. Oldenhuis, Alexander C. Eldredge, Jingjing Shen, Fnu Naorem Nihesh, Melissa B. Lodoen, Zhibin Guan, and Aaron P. Esser-Kahn. ACS Central Science. 2018, 4, pp 982-995. July 2, 2018. DOI: 10.1021/acscentsci.8b00218.
  12. PEG-Peptide Conjugates. Ian W Hamley. Biomacromolecules. 2014. April 1, 2014. DOI: 10.1021/bm500246w.
  13. Site-Dependent Degradation of a Non-Cleavable Auristatin-Based Linker-Payload in Rodent Plasma and Its Effect on ADC Efficacy. Magdalena Dorywalska, Pavel Strop, Jody A. Melton-Witt, Adela Hasa-Moreno, Santiago E. Farias, Meritxell Galindo Casas, Kathy Delaria, Victor Lui, Kris Poulsen, Janette Sutton, Gary Bolton, Dahui Zhou, Ludivine Moine, Russell Dushin, Thomas-Jaume Pons, Arvind Rajpal. Plos One. 2015, 10 (7) e0132282. July 10, 2015. DOI: 10.1371/journal.pone.0132282.
  14. A Synthetic Virus-Like Particle Streptococcal Vaccine Candidate Using B-Cell Epitopes from the Proline-Rich Region of Pneumococcal Surface Protein A. Marco Tamborrini, Nina Geib, Aniebrys Marrero-Nodarse, Maja Jud, Julia Hauser, Celestine Aho, Araceli Lamelas, Armando Zuniga, Gerd Pluschke, Arin Ghasparian and John A. Robinson. Vaccines. 2015, 3 (4), pp 850-874, October 16, 2015. DOI: 10.3390/vaccines3040850.
  15. Nanoallergens: A multivalent platform for studying and evaluating potency of allergen epitopes in cellular degranulation. Peter E Deak, Maura R Vrabel, Vincenzo J Pizzuti, Tanyel Kiziltepe, and Basar Bilgicer. Experimental Biology and Medicine. 2016, 0 pp 1-11. April 13, 2016. DOI: 10.1177/1535370216644533.
  16. Control of strand registry by attachment of PEG chains to amyloid peptides influences nanostructure. Valeria Castelletto, Ge Cheng, Steve Furzeland, Derek Atkinsb and Ian W. Hamley. Soft matter. 2012, 8, pp 5434-5438. April 16, 2012. DOI:10.1039/C2SM25546D.
  17. Optimizing design parameters of a peptide targeted liposomal nanoparticle in an in vivo multiple myeloma disease model after initial evaluation in vitro. Jared F. Stefanick, David T. Omstead, Jonathan D. Ashley, Peter E. Deak, Nur Mustafaoglu, Tanyel Kiziltepe, Basar Bilgicer. Journal of Controlled Releases. 2019, 311-312 pp 190-200. August 29, 2019. https://doi.org/10.1016/j.jconrel.2019.08.033.
  18. Engineering peptide-targeted liposomal nanoparticles optimized for improved selectivity for HER2-positive breast cancer cells to achieve enhanced in vivo efficacy. Baksun Kim, Jaeho Shin, Junmin Wu, David T. Omstead, Tanyel Kiziltepe, Laurie E. Littlepage, Basar Bilgicer. Journal of Controlled Release. 2020. Volume 322, 10 June 2020, Pages 530-541. April 8, 2020. DOI: 10.1016/j.jconrel.2020.04.010
  19. High Density Display of an Anti-Angiogenic Peptide on Micelle Surfaces Enhances Their Inhibition of αvβ3 Integrin-Mediated Neovascularization In Vitro. Rajini Nagaraj, Trevor Stack, Sijia Yi, Benjamin Mathew, Kenneth R Shull, Evan A Scott, Mathew T Mathew and Divya Rani Bijukumar.Nanomaterials 2020, 10(3), 581;March 22, 2020. DOI: 10.3390/nano10030581
  20. Efficient capture of circulating tumor cells with low molecular weight folate receptor-specific ligands. Yingwen Hu, Danyang Chen, John V Napoleon, Madduri Srinivasarao, Sunil Singhal, Cagri A Savran, Philip S Low. Scientific Reports. 2022. May 20, 2022. https://doi.org/10.1038/s41598-022-12118-3

Applicable patents and legal notices are available at legal notices.

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