t-boc-N-amido-dPEG®₄-acid

t-boc-N-amido-dPEG®4-acid, product number 10220, is one of Quanta BioDesign's popular peptide synthesis products. Designed for use in Boc-based peptide chemical synthesis, PN10220 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 group removes relatively easily with trifluoroacetic acid (TFA).

PEGylation with dPEG® Products
PEGylation, the covalent addition of polyethylene glycol (PEG) to a molecule or surface, is a popular modification of many peptides because the amphiphilic nature of PEG increases the water solubility of hydrophobic peptides. Moreover, PEG imparts flexibility into a peptide chain. Also, PEG is non-antigenic and can act as a shield from the immune system, effectively hiding a potentially antigenic peptide from the immune system. Furthermore, the PEGylation of peptides increases the hydrodynamic volume of the conjugates. Consequently, injected PEGylated peptides stay in the bloodstream longer due to reduced renal clearance.

Traditional PEGs are dispersed polymers (Đ > 1.00), meaning that the PEG molecular weight and chain length are averages calculated from intractable mixtures of different sizes of PEG molecules. By contrast, Quanta BioDesign invented, manufactures, and sells only single molecular weight (i.e., discrete) PEG compounds (Đ = 1) under the dPEG® trade name. Discrete PEG products tremendously simplify analytical issues for PEGylated peptides without sacrificing any of the benefits of PEGylation.

Peptide Synthesis with t-boc-N-amido-dPEG®4-acid
While solid-phase peptide synthesis using the 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group is the most popular chemistry for peptide synthesis, there are good reasons to carry out solid-phase peptide synthesis using the tert-butyloxycarbonyl (Boc, t-Boc, or t-boc) protecting group. For example, the synthesis of depsipeptides requires the use of Boc chemistry because the ester linkages in the peptide chain are sensitive to base, which is needed to remove the Fmoc protecting group.

Furthermore, side group protection or modification in peptide synthesis requires the use of protecting groups orthogonal to the chemistry used to grow the peptide backbone. When Fmoc chemistry is used to elongate the peptide chain, it is common to use acid-labile protecting groups to protect the amino acid side chains; Boc can be used to protect the side chain of lysine, for example.

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)1. 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.

PN10220, t-boc-N-amido-dPEG®4-acid, is one of a series of Boc-protected amino-dPEG® acid products. To help you find the right peptide modification reagent for your product or application, we invite you to review our whole family of peptide modification products.

Application Reference:

Gates, Z. P.; Dhayalan, B.; Kent, S. B. H. Obviation of Hydrogen Fluoride in Boc Chemistry Solid Phase Peptide Synthesis of Peptide-αthioesters. Chem. Commun. 2016, 52(97), 13979–13982. https://doi.org/10.1039/C6CC07891E.

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