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.
Product number 10268, CBZ-N-amido-dPEG®4-acid, is a benzyl carbamate (Cbz) N-protected amino-dPEG®-acid that provides a short (17 atoms, 19.2 Å) single molecular weight discrete PEG (dPEG®) spacer. It can be used in peptide synthesis as well as in many other reactions. In peptide synthesis, removal of the Cbz protecting group is orthogonal to many other protecting groups.
The Cbz protecting group (also called the Z protecting group) is one of the most popular protecting groups for amines. It is stable to base and mildly acidic conditions. A variety of methods cleave the Cbz group. The most popular cleavage technique is hydrogenolysis using palladium black or palladium on carbon.
PEGylation with dPEG® Products
PEGylation refers to the covalent addition of polyethylene glycol (PEG) to a compound or surface. PEGylated compounds include proteins, peptides, dyes or other labels, and small molecule drugs. Peptide synthesis frequently employs PEGylation to enhance the solubility of the peptide, because the amphiphilic character of PEG imparts tremendous water solubility to peptides. Moreover, peptide PEGylation prolongs in vivo circulation of peptide conjugates by both increasing the peptide’s hydrodynamic volume and protecting the peptide from proteolysis. Additionally, PEGylation reduces or eliminates antigenicity of the conjugated peptide. Quanta BioDesign’s single molecular weight PEG products (known as “discrete PEG” and sold under the dPEG® trademark) provide all of the benefits of traditional, dispersed PEG without the analytical headache that comes from having an intractable mixture of conjugates, each with different PEG chain lengths.
PN10268 works well in peptide synthesis with either solution phase or solid-phase chemistry. Carbodiimide chemistry activates the carboxylic acid, which then conjugates to a free amine group either on the N-terminus of the peptide chain or on an amino acid side chain. The terminal amine of the dPEG® chain is exposed by removal of the Cbz protecting group, making the amine available for additional reactions as needed. Other synthetic processes (e.g., surface modification, supramolecular construction) requiring the attachment or insertion of a short PEG linker or spacer can employ PN10268 profitably also.
PN10268 is part of a line of similar products. We invite you to consider our entire range of Cbz-protected amino-dPEG®x-acid products whenever you need a single molecular weight PEG for your product. If you need bulk product in a larger package size than our standard sizes, please contact us for a quote. Our commercial capabilities permit us to manufacture this product at any scale that you need.
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