Fmoc-N-amido-dPEG®₁₂-TFP ester (QBD-11006)

Description

Fmoc-N-amido-dPEG®12-TFP ester, product number QBD-11006 contains an Fmoc-protected amine on one end of a medium-length (40 atoms), single molecular weight, discrete-chain-length polyethylene glycol (dPEG®) spacer and the tetrafluorophenyl (TFP) ester of a propionic acid group on the other end. This product is ready for the direct introduction of a water-soluble, amphiphilic spacer into a peptide chain. The Fmoc protecting group on the N-terminus of the molecule cleaves easily with standard peptide chemistry.

Fmoc-N-amido-dPEG®12-TFP ester permits our customers to insert a dPEG® spacer into a peptide chain using standard Fmoc chemistry without the need to activate the acid terminus for conjugation. The product works equally well in solid-phase and solution-phase synthetic processes. In aqueous solutions, TFP esters are more hydrolytically stable than NHS esters and have an optimum pH range of 7.5 – 8.0 for conjugation. The dPEG® linker attaches at the N-terminal end of the peptide chain or on the free amine side chain of amino acids such as lysine. Additional peptide synthesis can be carried out to extend the peptide further, creating a peptide with a flexible, hydrophilic linker or spacer in the middle or joining two different peptides across the dPEG® bridge. In addition, the dPEG® chain can provide spacing in a synthetic construct where steric hindrance is a problem. Amphiphilic, non-immunogenic dPEG® increases the hydrodynamic volume and improves the water solubility of the conjugate while remaining soluble in organic solvents. The Fmoc protecting group is removed easily with a solution of piperidine in N,N-dimethylformamide (DMF).

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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.