Lysine Dendrons

Lysine Dendrons

Published on 02/12/2016

We now offer a series of Lysine dendrons for chemoselective functionalization of molecules containing carbonyl groups. These multivalent molecules carry diverse types of moieties, such as amine- or hydroxyl-groups, DOTA chelators or triphenylphosphonium (TPP) cations.

Dendronization is a synthetic method by which functional materials with specific architectures and useful new properties can be created.

We now offer several lysine dendrons equipped with a hydrazide functional group at the focal point/C-terminus for chemoselective conjugation to molecules bearing carbonyl groups. The conjugation can be performed with (or without) subsequent reduction of the hydrazone bond by NaBH4.

For your convenience, we offer a selection of Lys dendrons with spacer arms of different lengths (LS-3610, LS-3620, LS-3630). The terminal lysine residues can be further functionalized with amino-reactive molecules.

Moreover, we also offer a lysine dendron bearing several serine residues (LS-3640). By selective conjugation of this building block to peptides or polymers using the hydrazone ligation technique, multiple Ser residues can be incorporated into the target molecule, thus multiplying the number of reactive functional groups. Furthermore, these Ser residues can be converted to glyoxylic acid by periodate oxidation with NaIO4, thus creating multiple attachment sites for payloads with aldehyde-reactive groups.

Dendron and Dendrimer structure.

A further variant of our new dendrons is a DOTA-functionalized derivative (LS-3600). Conjugation of this dendron to peptide or polymer carrier molecules facilitates delivery of paramagnetic ions (Gd3+; Mn2+) or radioactive isotopes. Applications include the targeted delivery of MR contrast agents (e.g. Gd3+) and radioimmunotherapy.

Lastly, we included a triphenylphosphonium (TPP)-bearing dendron into our portfolio (LS-3650). This type of building block was designed for the targeted delivery of peptides, polymers and different drugs to mitochondria.

Our new dendrons (in the form of hydrazides) can be applied for the modification of synthetic or natural polymers containing reactive aldehyde groups (peptides must first be modified by oxidation of Ser or Thr residues). The dendrons can for example be applied for the design of gene delivery systems or for modifying the surface properties of polymers. The conjugation process can be performed using the hydrazone ligation approach with (or without) subsequent reduction of the resulting hydrazone bond by NaBH4. We can provide all necessary protocols.

 

→ Would you like to synthesize your own custom hydrazide-bearing dendrons? Use our Hydrazone Resin for convenient access to these structures.

References:

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