Description

m-dPEG^®₃₆-MAL, product number QBD-10931, is a sulfhydryl-reactive, single molecular weight, with a long (116 atoms, 137.2 Å), discrete-chain-length PEG (dPEG^®). This product modifies surfaces and biomolecules with free thiol groups through the maleimide reactive group. The non-immunogenic, methyl-terminated dPEG® chain has no charge but adds water solubility and hydrodynamic volume to molecules to which it is conjugated.

The reaction of the maleimide end of m-dPEG^®₃₆-MAL, product number QBD-10931, with a sulfhydryl proceeds best at pH 6.5 – 7.5. Conduct the conjugation at the lowest reasonable pH within this range. Above pH 7.5, free amines compete with free thiols at the maleimide reaction site, which creates confusing results. Moreover, at higher pH values, the maleimide ring may open to form unreactive maleamic acid.

Possible uses for m-dPEG^®₃₆-MAL include the following:
Surface coating and passivation of thiolated nanoparticles;
Modification of cysteine residues on peptides, proteins, and other sulfhydryl-containing molecules to increase hydrophilicity and decrease immunogenicity;
Modification of cysteine residues on peptides, proteins, and other sulfhydryl-containing molecules to increase hydrodynamic volume and reduce or eliminate renal clearance of the modified compound;
Supramolecular construction (for example, of hydrogels); and,
As a probe of protein structure or enzymatic function.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). See all of the extensive references to the reactions of maleimides with a variety of compounds and applications, Hermanson, p.1174 (index for maleimides) and references therein.

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.

Description

m-dPEG®36-amine, product number QBD-10908, is a non-immunogenic, water-soluble chemical modification reagent. The product contains a single molecular weight, discrete-length polyethylene glycol (dPEG®) chain terminated on one end with a methyl group and on the other end with a reactive primary amine. The linker length is 109 atoms (130.0 Å). The amino group reacts with carboxylic acids (and their active esters), aldehydes, and ketones. Reacting the amino group with aldehydes or ketones forms a labile imine (Schiff base) that can be reduced to a secondary amine under mild conditions to provide greater stability to the conjugate. Reacting carboxylic acids or their active esters with m-dPEG®36-amine forms stable amide bonds. Uses for this product include passivating surfaces and coating biomolecules.

Biomolecules modified with m-dPEG®36-amine display enhanced water solubility, increased hydrodynamic volume, and reduced immunogenicity. This product reacts quickly with active esters of carboxylic acids (for example, NHS esters and TFP esters) to form amide bonds. Also, it forms amide bonds directly with carboxylic acids using the carbodiimide EDC.

m-dPEG®36-amine is potentially useful in numerous applications. Such applications include the following:
Passivating nanoparticle surfaces, including the surfaces of carbon nanotubes and graphene oxide;
Creating a non-immunogenic “”stealth”” coating for liposomes and micelles;
Increasing the hydrodynamic volume of small molecules, including peptides and antibody fragments; and,
Increasing the water solubility of hydrophobic molecules.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; IBSN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

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.

Description

Amino-dPEG®36-acid, product number QBD-10907, is a PEGylated amino acid. A primary amine group and a propionic acid group sit on opposite ends of a long (111 atoms, 132.7 Å), single molecular weight polyethylene glycol (PEG) spacer with a discrete chain length (dPEG®). The highly hydrophilic, discrete PEG spacer (Ð = 1) increases the hydrodynamic volume and imparts water solubility to conjugates that incorporate it. Moreover, Amino-dPEG®36-acid may benefit numerous applications, including peptide synthesis, peptide modification, surface modification, oligonucleotide sequencing, drug delivery, and small molecule modification.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

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.

PEG-Labeled Nucleotides and Nanopore Detection for Single Molecule DNA Sequencing by Synthesis. Shiv Kumar, Chuanjuan Tao, Minchen Chien, Brittney Hellner, Arvind Balijepalli, Joseph W. F. Robertson, Zengmin Li, James J. Russo, Joseph E. Reiner, John J. Kasianowicz & Jingyue Ju. Scientific Reports. 2012, 2 (684). September 21, 2012. DOI: 10.1038/srep00684.

Description

CBZ-N-amido-dPEG®36-acid, product number QBD-10906, is a benzyl carbamate (Cbz) N-protected amino-dPEG®-acid that provides a long (111 atoms, 132.7 Å), single molecular weight discrete PEG (dPEG®) spacer. It can be used in peptide synthesis to modify the side chain of lysine and in other forms of supramolecular construction. The Cbz protecting group is stable to acidic and basic conditions and is most easily removed using palladium black or palladium on carbon with hydrogen. This makes Cbz removal orthogonal to most other peptide synthesis deprotection reactions.

CBZ-N-amido-dPEG®36-acid works well in solution-phase synthesis. Carbodiimide activation, with or without an acylating agent, permits conjugation of the acid terminus of the dPEG® product to free amines. Other synthetic processes (e.g., surface modification, supramolecular construction) requiring the attachment or insertion of a medium-length PEG linker or spacer can employ CBZ-N-amido-dPEG®36-acid profitably also.

Specifications

Documents

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.

Description

“Fmoc-N-amido-dPEG®36-acid, product number QBD-10903, is one of a broad line of products designed for use in peptide synthesis. The long (112 atoms), flexible, 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 non-immunogenic dPEG®36 spacer increases the hydrodynamic volume and imparts water solubility to the conjugate molecule.

QBD-10903 permits our customers to insert a dPEG® spacer into a peptide chain using familiar Fmoc chemistry using solid phase or solution phase chemistry. However, due to the spacer’s length, it may work better in solution-phase syntheses. 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 is removed easily with a solution of piperidine in N,N-dimethylformamide (DMF).”

Specifications

Documents

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.

Lipo-Oligomer Nanoformulations for Targeted Intracellular Protein Delivery. Peng Zhang, Benjamin Steinborn, Ulrich Lachelt, Stefan Zahler, and Ernst Wagner. Biomacromolecules. 2017, June 26, 2017. DOI: 10.1021/acs.biomac.7b00666.

Flexible antibodies with nonprotein hinges. Daniel J. Capon, Naoki Kaneko, Takayuki Yoshimori, Takashi Shimada, Florian M. Wurm, Peter K. Hwang, Xiaohe Tong, Staci A. Adams, Graham Simmons, Taka-Aki Sato and Koichi Tanaka. The Japan Academy, Series B. 2011, 87 (9) pp 603-616. November 11, 2011. DOI: 10.2183/pjab.87.603.

A Systematic Analysis of Peptide Linker Length and Liposomal Polyethylene Glycol Coating on Cellular Uptake of Peptide-Targeted Liposomes. Jared F. Stefanick, Jonathan D. Ashley, Tanyel Kiziltepe, and Basar Bilgicer. ACS Nano. 2013, 7 (4) pp 2935–2947. February 19, 2013. DOI: 10.1021/nn305663e.

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.

PEG-Peptide Conjugates. Ian W Hamley. Biomacromolecules. 2014, 15 (5) pp 1543-1559. April 1, 2014. DOI: 10.1021/bm500246w.

Evaluation of Nonpeptidic Ligand Conjugates for SPECT Imaging of Hypoxic and Carbonic Anhydrase IX-Expressing Cancers. Peng-Cheng Lv, Karson S. Putt, and Philip S. Low. Bioconjugate Chemistry. 2016, 27, pp 1762-1769. June 30, 2016. DOI: 10.1021/acs.bioconjchem.6b00271.

Bioresponsive nanocarries for targeted intracellular delivery of proteins and peptides. Ruth Elisabeth and Johanna Roder. Dissertation zur Erlangung des Doktorgrades der Fakultat fur Chemie und Pharmazie der Ludwig-Maximilians-Universitat Munchen. 2016, pp 1-128.

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

Description

t-boc-N-amido-dPEG®36-acid, product number QBD-10902, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of an extended (111 atoms, 132.7 Å), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®36-acid can be used to insert a discrete PEG linker/spacer at the N-terminus of a peptide chain or to add a dPEG® onto the side chain of an amino acid such as lysine or ornithine. Insertion of t-boc-N-amido-dPEG®36-acid at the N-terminus of a peptide allows the creation of a flexible, hydrophilic bridge to the C-terminus of another peptide. The Boc protecting group cleaves easily under acidic conditions with, for example, TFA. This compound can also be used to modify amine-functionalized surfaces to passivate them with a hydrophilic spacer. Removal of the boc group with acid allows for functionalization of the surface with peptides, proteins, or small molecules.

Specifications

Documents

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.

Description

Amino-dPEG®36-OH, product number QBD-10869, also known as Amino-dPEG®36-alcohol, is a long (107 atoms, 129.0 Å), monodispersed PEGylation reagent designed to modify surfaces and biomolecules. One end of the molecule terminates with a primary amine, while the other end terminates with a primary alcohol group. This extremely hydrophilic PEGylation reagent reacts with carboxylate groups via the primary amine, leaving the hydroxy terminus free for functionalization and further reactions or as a hydrophilicity or charge modifier for the conjugate molecule.

The most common uses for Amino-dPEG®36-OH include modifying biomolecules and passivating surfaces with a highly hydrophilic coating. The primary amine on one end of the dPEG® linker reacts with carboxylates to form stable amide bonds and with aldehydes and ketones to form labile Schiff bases that can be reduced to secondary amines under mild conditions for greater stability. Conjugations with this molecule most commonly use the amine-carboxylate reaction with a carbodiimide such as EDC. Alternatively, activation of carboxylate as the NHS or TFP ester followed by reaction under slightly basic conditions also permits conjugation of the carboxylate and amino moieties.

Specifications

Documents

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.

Description

m-dPEG®36-OH, product number QBD-10728, is a chemical modification reagent. It consists of a methyl-terminated, water-soluble, non-immunogenic, single molecular weight, discrete polyethylene glycol (dPEG®) chain that terminates with a reactive hydroxy group. The hydroxy group can be functionalized with different groups that enable various types of reactions. Uses for m-dPEG®36-OH include surface passivation and biomolecule modification.

Specifications

Documents

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.

Temperature-Responsive Self-Assembled Monolayers of Oligo(ethylene glycol): Control of Biomolecular Recognition .Hadi M. Zareie , Cyrille Boyer , Volga Bulmus , Ebrahim Nateghi and Thomas P. Davis. ACS Nano. 2008, 2 (4) pp 757-765. April 4, 2008. 10.1021/nn800076h

Sequential Nucleophilic Substitutions Permit Orthogonal Click Functionalization of Multicomponent PEG Brushes. Jin Sha, Ethan S. Lippmann, Jason McNulty, Yulu Ma, and Randolph S. Ashton. Biomacromolecules. 2013, 14 (9) pp 3294–3303. August 13, 2013. DOI: 10.1021/bm400900r.

Description

Azido-dPEG®36-OH (Azido-dPEG®36-alcohol), product number QBD-10544, is a click chemistry reagent used to modify surfaces and biomolecules or to crosslink with other surfaces or biomolecules in supramolecular construction. This product consists of an azide and a terminal hydroxy group separated by a long (108 atoms), single molecular weight, discrete-length polyethylene glycol (dPEG®) chain. The terminal azide reacts in copper(I)-catalyzed, ruthenium-catalyzed, and strain-promoted azide-alkyne cycloaddition reactions (CuAAC, RuAAC, and SPAAC, respectively). If left unmodified, the alcohol group increases the water solubility and hydrodynamic volume of molecules and surfaces to which it is conjugated. Modifying the alcohol with a reactive group such as chloride, tosylate, or mesylate allows Azido-dPEG®36-OH to function as a crosslinker through subsequent chemical manipulations.

As a click chemistry reagent, azido-dPEG®36-OH can participate in CuAAC, RuAAC, and SPAAC reactions. Because Vector Laboratories’ dPEG® products are amphiphilic, these reactions can occur almost equally well in water or organic solvents. The primary alcohol group on the opposite end of the linker can be used as a neutrally charged functional group. In this function, the alcohol enhances the water solubility of the conjugate molecule. Alternatively, the alcohol group can be functionalized with reactive groups and used to modify the conjugate further. Thus, azido-dPEG®36-OH can be used in conjugations with biomolecules where organic solvents may damage the conjugate target. This product was published in a 2014 paper demonstrating high-throughput modifications of siRNA via CuAAC.

Specifications

Documents

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.

Application of Multivalent Interactions for Recognition Imaging and Delivery of Therapeutics. Saikat Manna. August 2016.

Description

m-dPEG®36-azide, product number QBD-10531, also known as azido-m-dPEG®36, is a monodispersed PEG product used in click chemistry applications. A non-reactive, charge-neutral methyl group and an alkyne-reactive azido group, respectively, terminate the two ends of the long (110 atoms), single molecular weight, discrete PEG (dPEG®) spacer. Both metal-catalyzed (Cu(I), Ru) azide-alkyne cycloaddition (CuAAC, RuAAC) and strain-promoted azide-alkyne cycloaddition (SPAAC) work with this product. Possible click chemistry-based applications for this product include the construction of dendrimers and hydrogels and the modification of alkyne-functionalized surfaces or biomolecules containing alkyne groups.

Specifications

Documents

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.