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Fmoc-N-amido-dPEG®₈-acid (QBD-10273)

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Description

Fmoc-N-amido-dPEG®8-acid, product number QBD-10273, is one of a broad line of products designed for use in peptide synthesis. The short (28 atoms), discrete PEG (dPEG®) spacer is functionalized with a propionic acid group on one end and Fmoc-protected amine on the other. The compound 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®8 spacer imparts water solubility to the peptide to which it is conjugated.

QBD-10273 permits our customers to insert a short (28 atoms) dPEG® into a peptide chain using familiar Fmoc chemistry. The product works equally well in solid phase and solution phase synthetic processes. The dPEG® can be inserted at either end of the peptide chain or in the middle of two amino acid sequences to provide a flexible spacer between distinct functional peptides. Additionally, the short dPEG® spacer can be used to provide extra distance in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® means that the construct will gain some degree of 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 Size100 mg, 1000 mg
Molecular Weight663.75; single compound
Chemical formulaC₃₄H₄₉NO₁₂
CAS756526-02-0
Purity> 98%
SpacersdPEG® Spacer is 28 atoms and 32.2 Å
ShippingAmbient
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

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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A Non-Chromatographic Method for the Purification of a Bivalently Active Monoclonal IgG Antibody from Biological Fluids. Basar Bilgicer, Samuel W. Thomas III, Bryan F. Shaw, George K. Kaufman, Vijay M. Krishnamurthy, Lara A. Estroff, Jerry Yang, and George M. Whitesides. Journal of the American Chemical Society. 2009, 131 (26) pp 9361–9367. June 17, 2009. DOI: 10.1021/ja9023836.

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A Synthetic Trivalent Hapten that Aggregates anti-2,4-DNP IgG into Bicyclic Trimers. Başar Bilgiçer, Demetri T. Moustakas, and George M. Whitesides. Journal of the American Chemical Society. 2007, 129 (12) pp 3722-3728. February 28, 2007. DOI: 10.1021/ja067159h.

Determination of bacterial viability by selective capture using surface-bound siderophores. Mark L. Wolfenden, Rama M. Sakamuri, Aaron S. Anderson, Lakshman Prasad, Jurgen G. Schmidt, Harshini Mukundan. Advances in Biological Chemistry. 2012, 2 (4) pp 396-402 September 30, 2012. DOI: 10.4236/abc.2012.24049.

Synthetic Allergen Design Reveals the Significance of Moderate Affinity Epitopes in Mast Cell Degranulation. Michael W. Handlogten, Tanyel Kiziltepe, Nathan J. Alves, and Basar Bilgicer. ACS Chemical Biology. 2012, 7 (11) pp 1796–1801. August 10, 2012. DOI: 10.1021/cb300193f.

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.

Novel solubility-switchable MRI agent allows the noninvasive detection of matrix metalloproteinase-2 activity In vivo in a mouse model. Rejean Lebel, Beata Jastrzebska, Helene Therriault, Marie-Michele Cournoyer, J. Oliver McIntyre, Emanuel Escher, Witold Neugebauer, Benoit Paquette, and Martin Lepage. Magnetic Resonance in Medicine. 2008, 60 (5) pp 1056–1065. October 27, 2008. DOI: 10.1002/mrm.21741.

Design of a Heterotetravalent Synthetic Allergen That Reflects Epitope Heterogeneity and IgE Antibody Variability to Study Mast Cell Degranulation. Michael W. Handlogten, Tanyel Kiziltepe and Basar Bilgicer. Biochem. J. 2013, 449 (1) pp 91–99. January 1, 2013. DOI: 10.1042/BJ20121088.

Design of a Heterobivalent Ligand to Inhibit IgE Clustering on Mast Cells. Michael W. Handlogten, Tanyel Kiziltepe, Demetri T. Moustakas, and Basxar Bilgicer. Chemistry & Biology. 2011, 18 (9) pp 1179–1188. September 23, 2011. DOI: 10.1016/j.chembiol.2011.06.012.

Design of a Heterobivalent Inhibitor of Allergy and More Physiologically Relevant Allergy Models. Michael William Handlogten. University of Notre Dame. 2013, March 28, 2013.

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Positron Emission Tomographic Imaging of Copper 64– and Gallium 68–Labeled Chelator Conjugates of
the Somatostatin Agonist Tyr3-Octreotate. Jessie R. Nedrow, Alexander G. White, Jalpa Modi, Kim Nguyen, Albert J. Chang and Carolyn J. Anderson. Molecular Imaging. 2014, 13 pp 1-13. Decebmer 14, 2014. DOI: 10.2310/7290.2014.00020.

Peripheral administration of a long-acting peptide OT receptor agonist inhibits fear induced freezing. Meera E. Modi, Mark J. Majchrzak, Kari R. Fonseca, Angela Doran, Sarah Osgood, Michelle Vanase-Frawley, Eric Feyfant, Heather McInnes, Ramin Darvari, Derek L. Buhl, and Natasha M. Kablaoui. JPET. 2016, 357 (3). May 23, 2016. DOI: 10.1124/jpet.116.232702.

Designer covalent heterobivalent inhibitors prevent IgE-dependent responses to peanut allergen. Peter E. Deak, Baksun Kim, Amina Abdul Qayum, Jaeho Shin, Girish Vitalpur, Kirsten M. Kloepfer, Matthew J. Turner, Neal Smith, Wayne G. Shreffler, Tanyel Kiziltepe, Mark H. Kaplan, and Basar Bilgicer. 2019. April 8, 2019. DOI: 10.1073/pnas.1820417116

Membrane-Fusogen Distance Is Critical for Efficient Coiled-Coil-Peptide-Mediated Liposome Fusion. Geert A. Daudey, Harshal R. Zope, Jens Voskuhl, Alexander Kros , and Aimee L. Boyle. Langmuir. 2017, 33 (43) pp 12443-12452. 10/5/2017. DOI: 10.1021/acs.langmuir.7b02931.

Applicable patents and legal notices are available at legal notices.

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