CBZ-N-amido-dPEG®36-acid, product number 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 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. Cbz can be cleaved by a variety of methods. The most popular cleavage method 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 a peptide’s solubility in water. 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.
CBZ-N-amido-dPEG®36-acid works well in peptide synthesis using solution-phase chemistry. Activation of the product using carbodiimide chemistry allows for functionalization of CBZ-N-amido-dPEG®36-acid with an acylating agent such as N-hydroxysuccinimide (NHS) or 2,3,5,6-tetrafluorophenol (TFP). The worked-up activated ester then reacts with free amine groups on the N-terminus of the peptide chain or an amino acid side chain. The terminal amine of the dPEG® product 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 long PEG linker or spacer can employ CBZ-N-amido-dPEG®36-acid profitably also.
CBZ-N-amido-dPEG®36-acid is One of a Range of Similar Products
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