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

t-boc-N-amido-dPEG®24-acid, product number QBD-10760, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of an extended (76 atoms), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®24-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®24-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

t-boc-N-amido-dPEG®12-acid, product number QBD-10760, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of a medium-length (40 atoms), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®12-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®12-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

t-boc-N-amido-dPEG®8-acid, product number QBD-10760, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of a short (28 atoms), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®8-acid can be used to insert a discrete PEG linker/spacer at the N-terminus of a peptide chain or to add a short dPEG® onto the side chain of an amino acid such as lysine or ornithine. Insertion of t-boc-N-amido-dPEG®8-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.

Covalently deposited dyes: a new chromogen paradigm that facilitates analysis of multiple biomarkers in situ. William A Day, Mark R Lefever, Robert L Ochs, Anne Pedata, Lauren J Behman, Julia Ashworth-Sharpe, Donald D Johnson, Eric J May, James G Grille, Esteban A Roberts, Jerry W Kosmeder, and Larry E Morrison. Laboratory Investigation. 2016, 00 pp 1-10. November 21, 2016. DOI: 10.1038/labinvest.2016.115.

Description

t-boc-N-amido-dPEG®4-OH, product number QBD-10250, is a short, monodispersed PEGylation reagent with an alcohol on one end of the single molecular weight, discrete-length PEG (dPEG®) chain and a boc-protected amine on the other end. This product is useful for building novel constructs with dPEG® linkers. This product also permits supramolecular construction and unique side-chain modifications of amino acid residues in peptides.

The terminal alcohol of t-boc-N-amido-dPEG®4-OH can be transformed easily into a different functional group such as an aldehyde or acid. Moreover, the hydroxy group reacts with halide-functionalized compounds to form new products. For example, by reacting propargyl bromide with the terminal hydroxy group in the presence of a base, a dPEG® product with an aliphatic alkyne is formed. Thus, t-boc-N-amido-dPEG®4-OH is a building block for new constructs that incorporate a discrete-length PEGylation product.
The boc-protected amine easily deprotects with trifluoroacetic acid or another acid. The exposed amine may be reacted further or left unmodified.

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.

Effects of linker variation on the in vitro and in vivo characteristics of an In-labeled RGD peptide, Ingrid Dijkgraaf, Shuang Liu, John A.W. Kruijtzer, Annemieke C. Soede, Wim J.G. Oyen, Rob M.J. Liskamp, Frans H.M. Corstens, Otto C. Boerman. Nuclear Medicine and Biology. 2007, 1 (34), pp 29-35, January 2007. DOI: 10.1016/j.nucmedbio.2006.10.006.

Description

t-boc-N-amido-dPEG®3-amine, product number QBD-10225, is a monoprotected, diamine-functionalized, homobifunctional crosslinking PEGylation reagent containing a short, single molecular weight PEG linker. One of the two primary carboxylate-reactive groups is protected as a tert-butyl carbamate. Both ends of the molecule react with carboxylic acids, aldehydes, and ketones. Carboxylic acids react with this product to form amide bonds, while reactions with aldehydes and ketones form Schiff bases that are reducible to secondary amines. The mono-protected end of the molecule gives the user tighter control over crosslinking.

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.

Design and Synthesis of Bis-Biotin-Containing Reagents for Applications Utilizing Monoclonal Antibody-Based Pretargeting system with Streptavidin Mutants, D. Scott Wibur, Steven I. Park, Ming-Kuan Chyan, Feng Wan, Donald K. Hamlin, Jaideep Shenoi, Yukang Lin, Shani M. Wilbur, Franz Buchegger, Anastasia Pantelias, John M. Pagel, and Oliver W. Press. Bioconjugate Chem. 2010, 21 (7), pp 1225–1238. July 2, 2010. DOI: 10.1021/bc100030q.

Novel Nanoassemblies Composed of Squfalenoyl—Paclitaxel Derivatives: Synthesis, Characterization, and Biological Evaluation, Franco Dosio, L. Harivardhan Reddy, Annalisa Ferrero, Barbara Stella, Luigi Cattel, and Patrick Couvreur. Bioconjugate Chem. 2010, 21 (7), pp 1349–1361. July 2, 2010. DOI: 10.1021/bc100154g.

A continuous fluorescence displacement assay for BioA: An enzyme involved in biotin biosynthesis. Daniel J. Wilson, Ce Shi, Benjamin P. Duckworth, Joseph M. Muretta, Ujjini Manjunatha, Yuk Y. Sham, David D. Thomas, and Courtney C. Aldrich. Analytical Biochemistry. 2011, 416 (1) pp 27-38. September 2011. DOI:10.1016/j.ab.2011.05.003.

Thiol-Mediated Anchoring of Ligands to Self-Assembled Monolayers for Studies of Biospecific Interactions. Kunal V. Gujraty, Randolph Ashton, Sridhar R. Bethi, Sandesh Kate, Christopher J. Faulkner, G. Kane Jennings, and Ravi S. Kane. Langmuir. 2006, 22 (24) pp 10157–10162. October 19, 2006.DOI: 10.1021/la0621463.

Design, Synthesis, and Validation of a Branched Flexible Linker for Bioactive Peptides. Martina E. Bowen, Yasunari Monguchi, Rajesh Sankaranarayanan, Josef Vagner, Lucinda J. Begay, Liping Xu, Bhumasamudram Jagadish, Victor J. Hruby, Robert J. Gillies, and Eugene A. Mash. J. Org. Chem. 2007, 72 (5) pp 1675–1680. February 6, 2007. DOI: 10.1021/jo062276g.

Time-resolved fluorescence resonance energy transfer and surface plasmon resonance-based assays for retinoid and transthyretin binding to retinol-binding protein 4. Orzala Sharif, Huiyong Hu, Heath Klock, Eric N. Hampton, Edward Nigoghossian, Mark W. Knuth, Jason Matzen, Paul Anderson, Richard Trager, Tetsuo Uno, Richard J. Glynne, Sassan M. Azarian, Jeremy S. Caldwell , Achim Brinker. Analytical Biochemistry. 2009, 392, (2) PP 162–168. September 15 , 2009. doi.org/10.1016/j.ab.2009.05.038.

Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand. Wenhao Liu, Andrew B. Greytak, Jungmin Lee, Cliff R. Wong, Jongnam Park, Lisa F. Marshall, Wen Jiang, Peter N. Curtin, Alice Y. Ting, Daniel G. Nocera, Dai Fukumura, Rakesh K. Jain and Moungi G. Bawendi. J. Am. Chem. Soc. 2010, 132 (2) pp 472–483. December 21, 2009. DOI: 10.1021/ja908137d.

Description

t-boc-N-amido-dPEG®4-acid, product number QBD-10220, is a boc-protected amino-PEG-acid designed for use in Boc-based peptide chemical synthesis. This product allows the insertion of a short hydrophilic PEG linker into a growing PEG chain or on an amino acid side chain in the peptide. The Boc protecting group removes relatively easily under acidic conditions.

t-boc-N-amido-dPEG®4-acid can be used in Boc solid-phase peptide synthesis to insert a discrete PEG linker/spacer at the N-terminus of a peptide chain or to add a short (16 atoms) dPEG® onto the side chain of an amino acid such as lysine or ornithine. The Boc protecting group can be cleaved using TFA, HF, or trifluoromethane sulfonic acid (TFMSA). Insertion of t-boc-N-amido-dPEG®4-acid at the N-terminus of a peptide allows the creation of a flexible, hydrophilic bridge to the C-terminus of another peptide.

Specifications

Documents

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.

Description

t-boc-N-amido-dPEG®11-amine, product number QBD-10172, is a diamine-functionalized, homobifunctional, monodisperse PEGylation reagent with one of the two primary amine-reactive groups protected as a tert-butyl carbamate. Both ends of the molecule react with carboxylic acids, aldehydes, and ketones. Carboxylic acids react with this product to form amide bonds, while reactions with aldehydes and ketones form Schiff bases that are reducible to secondary amines. The mono-protected end of the molecule gives the user greater control over when and where to react the primary amine following deprotection.

The free amine end of the molecule reacts with carboxylic acids or their active esters. With carboxylic acids, a carbodiimide such as EDC directly couples the amine to the acid, forming the amide. With active esters (for example, NHS or TFP esters) of carboxylic acids, the reaction runs in organic solvents or aqueous buffers using conventional chemistry. After the free amine has reacted, the protected end of the molecule is deprotected with trifluoroacetic acid (TFA) or some other suitable organic acid and then coupled to a carboxylate or active ester as above.

Scientific publications using t-boc-N-amido-dPEG®11-amine describe the following uses for this compound:
Immobilization of enzymes and antibodies;
Construction of supramolecular assemblies;
Engineering of quantum dots; and,
Development of biomolecular sensors.

Specifications

Documents

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. Oriented Immobilization of Fab Fragments by Site-Specific Biotinylation at the Conserved Nucleotide Binding Site for Enhanced Antigen Detection. Nur Mustafaoglu, Nathan J. Alves, and Basar Bilgicer. Langmuir. 2015, 31 (35) pp 9728-9736. August 14, 2015. DOI: 10.1021/acs.langmuir.5b01734.

3. Novel Nanoassemblies Composed of Squalenoyl—Paclitaxel Derivatives: Synthesis, Characterization, and Biological Evaluation, Franco Dosio, L. Harivardhan Reddy, Annalisa Ferrero, Barbara Stella, Luigi Cattel, and Patrick Couvreur. Bioconjugate Chem. 2010, 21 (7), pp 1349–1361. July 2, 2010. DOI: 10.1021/bc100154g.

4. Development of an oligo (ethylene glycol)-based SPR immunosensor for TNT detection. Yutaka Mizuta, Takeshi Onodera, Praveen Singh, Kiyoshi Matsumoto, Norio Miura, Kiyoshi Toko. Biosensors and Bioelectronics. 2008. 24 (2). Pp. 191-197. DOI:10.1016/j.bios.2008.03.042.

5. 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 1, 2012. DOI: 10.1021/la301887s.

6. Immobilization of Actively Thromboresistant Assemblies on Sterile Blood-Contacting Surfaces. Zheng Qu, Venkat Krishnamurthy, Carolyn A. Haller, Brent M. Dorr, Ulla M. Marzec, Sawan Hurst, Monica T. Hinds, Stephen R. Hanson, David R. Liu, and Elliot L. Chaikof. Adv. Healthcare Mater. 2013. March 23, 2013. DOI: 10.1002/adhm.201300110.

7. 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.

8. Nanotube-assisted protein deactivation. Amit Joshi, Supriya Punyani, Shyam Sundhar Bale, Hoichang Yang, Theodorian Borca-Tasciuc and Ravi S. Kane. Nature Nanotechnology. 2008, 3 pp 41 – 45. December 9, 2007. doi:10.1038/nnano.2007.386

9. Biomimetic Ligands for Immunoglobulin-M Purification. Satyen Gautam. Doctoral Dissertation, National University of Singapore: Singapore, April 12, 2010. DOI: www.scholarbank.nus.edu.sg/handle/10635/22872.

10. Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand. Wenhao Liu, Andrew B. Greytak, Jungmin Lee, Cliff R. Wong, Jongnam Park, Lisa F. Marshall, Wen Jiang, Peter N. Curtin, Alice Y. Ting, Daniel G. Nocera, Dai Fukumura, Rakesh K. Jain and Moungi G. Bawendi. J. Am. Chem. Soc. 2010, 132 (2) pp 472–483. December 21, 2009. DOI: 10.1021/ja908137d.

Description

t-boc-N-amido-dPEG®12-OH, product number QBD-10171, is a medium-length, monodispersed PEGylation reagent. This reagent terminates with alcohol on one end of the single molecular weight, discrete-length PEG (dPEG®) chain and a boc-protected amine on the other end. QBD-10171 is useful as a building block for other constructs that contain a discrete PEG in them.

This product is useful for building unique constructs with dPEG® linkers. This product also permits supramolecular construction and unique side-chain modifications of amino acid residues in peptides. The terminal alcohol of t-boc-N-amido-dPEG®12-OH reacts readily with isothiocyanate groups and the active esters of carboxylic acids. Moreover, it can be transformed easily into different functional groups, including aldehydes, azides, amines, and aliphatic alkynes. For example, reacting propargyl bromide with the terminal hydroxy group in the presence of a base forms a dPEG® product with an aliphatic alkyne for use in click chemistry reactions. Thus, t-boc-N-amido-dPEG®12-OH is a building block for new constructs that incorporate a discrete-length PEGylation product.

The boc-protected amine easily deprotects with trifluoroacetic acid or another acid. The exposed primary amine may be left unmodified or reacted with appropriate groups for further construction.

Specifications

Documents

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.
   
   

Description

t-boc-N-amido-dPEG®23-amine, product number QBD-10093, is a monoprotected, homobifunctional, discrete PEG (dPEG®) crosslinker. The amine groups react with carboxylic acids, active esters (e.g., NHS, TFP, PFP) of carboxylic acids, aldehydes, and ketones. The tert-butyl carbamate (t-boc) protecting group is removed quickly and easily under mild conditions. The dPEG® linker provides flexibility and water solubility to conjugate molecules. Examples of uses for this product include graphene quantum dot engineering, antibody and enzyme immobilization, development of biomolecular sensors, and construction of supramolecular assemblies.

Specifications

Documents

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.