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Fmoc-N-amido-dPEG®₂-acid (QBD-10243)

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Fmoc-N-amido-dPEG®2-acid, product number QBD-10243, is one of a broad line of products designed for use in peptide synthesis. The short (16 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®2 spacer imparts water solubility to the peptide to which it is conjugated.

Description

Fmoc-N-amido-dPEG®2-acid, product number QBD-10243, is a peptide synthesis product used to introduce a short (10 atoms), hydrophilic spacer into a peptide chain using standard peptide chemistry. The Fmoc protecting group can be removed using standard peptide chemistry.

Fmoc-N-amido-dPEG®2-acid, QBD-10243, works well in solid-phase and solution-phase synthetic processes. The dPEG® can be joined to the N-terminal end of a peptide chain. After removal of the Fmoc protecting group, further synthesis can be carried out to create a peptide with a flexible hinge. The peptide sequences on either side of the dPEG® spacer can be identical or different.

In addition, the short dPEG® linker can provide spacing between two units in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® means that the construct will gain water solubility while remaining soluble in an organic solvent. The Fmoc protecting group removes easily with a solution of piperidine in N,N-dimethylformamide (DMF).

Specifications

Unit Size1000 mg
Molecular Weight399.44; single compound
Chemical formulaC₂₂H₂₅NO₆
CAS872679-70-4
Purity> 98%
SpacersdPEG® Spacer is 10 atoms and 10.9 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.

Functional PEG-Modified Thin Films for Biological Detection. Aaron S. Anderson, Andrew M. Dattelbaum, Gabriel A. Montano, Dominique N. Price, Jurgen G. Schmidt, Jennifer S. Martinez, W. Kevin Grace, Karen M. Grace, and Basil I. Swanson. Langmuir. 2008, 24 (5), pp 2240–2247. January 30, 2008. DOI: 10.1021/la7033438.

Polyproline-Rod Approach to Isolating Protein Targets of Bioactive Small Molecules: Isolation of a New Target of Indomethacin. Shin-ichi Sato, Youngjoo Kwon, Shinji Kamisuki, Neeta Srivastava, Quian Mao, Yoshinori Kawazoe, and Motonari Uesugi. J. Am. Chem. Soc. 2007, 129 (4), pp 873–880. January 4, 2007. DOI: 10.1021/ja0655643.

Oriented Surface Immobilization of Antibodies at the Conserved Nucleotide Binding Site for Enhanced Antigen Detection. Nathan J Alves, Tanyel Kiziltepe, and Basar Bilgicer. Langmuir. 2012, 28 (25) pp 9640-9648. May 21, 2012. DOI: 10.1021/la301887s.

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.

Selective photocrosslinking of functional ligands to antibodies via the conserved nucleotide binding site. Nathan J. Alves, Matthew M. Champion, Jared F. Stefanick, Michael W. Handlogten, Demetri T. Moustakas, Yunhua Shi, Bryan F. Shawd, Rudolph M. Navari, Tanyel Kiziltepe, Basar Bilgicer. Biomaterials. 2013, 34 (22) pp 5700–5710. April 16, 2013. DOI:.org/10.1016/j.biomaterials.2013.03.082.

Design, Synthesis and Evaluation of a Neurokinin 1 Receptor-Targeted Near IR Dye for Fluorescence Guided Surgery of Neuroendocrine Cancers. Ananda Kumar Kanduluru, Madduri Srinivasarao, and Philip S. Low. Bioconjugate Chemistry. 2016, pp 1-20. August 16, 2016. DOI: 10.1021/acs.bioconjchem.6b00374.

One-Pot Isolation of a Desired Human Genome Fragment by Using a Biotinylated pcPNA/S1 Nuclease Combination. Arivazhagan Rajendran , Narumi Shigi, Jun Sumaoka, and Makoto Komiyama. Biochemistry. 2018, 57, pp 2908-2912. May 3, 2018. DOI: 10.1021/acs.biochem.8b00202.

Stapled, Long-Acting Glucagon-like Peptide 2 Analog with Efficacy in Dextran Sodium Sulfate Induced Mouse Colitis Models. Peng-Yu Yang , Huafei Zou, Candy Lee, Avinash Muppidi, Elizabeth Chao, Qiangwei Fu, Xiaozhou Luo, Danling Wang, Peter G. Schultz, and Weijun Shen. Journal of Medicinial Chemistry. 2018, 61, pp 3218-3223. March 12, 2018. DOI: 10.1021/acs.jmedchem.7b00768.

Evaluation of the Pharmacokinetic Effects of Various Linking Group Using the 111In-DOTA-X-BBN(7−14)NH2 Structural Paradigm in a Prostate Cancer Model. Jered C. Garrison, Tammy L. Rold, Gary L. Sieckman, Farah Naz, Samantha V. Sublett, Said Daibes Figueroa, Wynn A. Volkert and Timothy J. Hoffman. Bioconjugate Chem. 2008, 19 (9) pp 1803–1812. August 20, 2008. DOI: 10.1021/bc8001375.

PEG-Peptide Conjugates. Ian W Hamley. Biomacromolecules. 2014. April 1, 2014. DOI: 10.1021/bm500246w.

Dual-receptor targeted strategy in nanoparticle design achieves tumor cell selectivity through cooperativity. Jared Francis Stefanick, David Thomas Omstead, Tanyel Kiziltepeabc and Basar Bilgicer. Nanoscale. 2019. Fenruary 17, 2019. DOI: 10.1039/C8NR09431D

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.

Design and Evaluation of Novel Polymyxin Fluorescent Probes. Bo Yun , Kade D. Roberts, Philip E. Thompson, Roger L. Nation, Tony Velkov, and Jian Li. Sensors. 2017, 17 (11) pp 2598. 11/11/2017. DOI: 10.3390/s17112598.

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

In vivo evaluation of CD38 and CD138 as targets for nanoparticle-based drug delivery in multiple myeloma. David T. Omstead, Franklin Mejia, Jenna Sjoerdsma, Baksun Kim, Jaeho Shin, Sabrina Khan, Junmin Wu, Tanyel Kiziltepe, Laurie E. Littlepage & Basar Bilgicer. Journal of Hematology & Oncology. 2020. 13, Article number: 145 (2020). 11/02/20. DOI: 10.1186/s13045-020-00965-4

Applicable patents and legal notices are available at legal notices.

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