DBCO-dPEG®₃₆-TFP ester

DBCO-dPEG®36-TFP ester, product number 10598, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a long, flexible, hydrophilic spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds, while the dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC). A single molecular weight, discrete polyethylene glycol (dPEG®) spacer separates the two functional groups and imparts hydrophilicity to the crosslinker.

Copper-Free Click Chemistry

Carolyn Bertozzi and coworkers published their discovery of SPAAC, also known as "copper-free click chemistry," in 2004. This discovery improved the click chemistry toolbox by eliminating toxic copper catalysts, thus permitting the labeling of live cells through a genuinely bioorthogonal reaction. Since the original publication, multiple improvements in strained cyclooctyne reagents resulted in the development of DBCO as a nearly perfect azide partner for SPAAC.

TFP Esters vs. NHS Esters

TFP esters offer many advantages over traditional N-hydroxysuccinimide (NHS) esters. TFP esters are more stable to hydrolysis in aqueous media than NHS esters, even at higher pH ranges. Moreover, our in-house testing shows that at optimum pH, TFP esters label primary amines more readily than NHS esters. Published research by Wang et al. supports this finding.

PEGylation with dPEG® Reagents

Conventional PEG reagents are dispersed (properly, non-uniform) polymers (Đ > 1). Dispersed PEG polymers contain a complex mixture of different chain lengths and molecular weights in a Poisson distribution.

OurdPEG® reagents are superior to traditional polymeric polyethylene glycol (PEG) reagents. In contrast to conventional PEG reagents, each dPEG® reagent from Quanta BioDesign, Ltd contains a single PEG compound. We synthesize and build up our dPEG® reagents from high purity starting materials rather than polymerization. Thus, our dPEG® products are monodispersed (Ð = 1). Our dPEG® linkers simplify the analysis of complex biological and biochemical constructs because each dPEG® crosslinker has a discrete chain length and single molecular weight.

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