dPEG®₂₄-SATA (S-acetyl-dPEG®₂₄-NHS ester) (QBD-10188)

Description

dPEG®24-SATA, also known as S-acetyl-dPEG®24-NHS ester, product number QBD-10188, is one of Quanta BioDesign’s versions of the widely popular thiolation reagent N-succinimidyl-S-acetylthioacetate (SATA). The acetyl-protected thiol is separated from the N-hydroxysuccinimidyl (NHS) ester by an amphiphilic, discrete polyethylene glycol (dPEG®) spacer. The long, flexible dPEG®24 spacer adds water solubility to the product.

Thiolation is the process of adding a sulfhydryl group to a molecule. Bioconjugation frequently employs thiolation because the reactions to install thiol groups on molecules or to react molecules with sulfhydryl groups are simple and often chemoselective.

The widely popular SATA reagent thiolates molecules with available amines via the NHS ester. Removal of the acetyl protecting group from the sulfhydryl permits crosslinking between the SATA-modified compound and a target molecule of interest that contains a thiol-reactive group, such as maleimide. Unfortunately, SATA is hydrophobic. Consequently, before use, SATA must be dissolved in a dry, water-miscible organic solvent.

Vector Laboratories’ dPEG®24-SATA inserts a single molecular weight spacer between the protected thiol and the NHS ester. The dPEG® spacer imparts water solubility to the molecule, allowing dPEG®24-SATA to dissolve and react in water without the need for an organic solvent. Also, the dPEG®24 spacer adds hydrodynamic volume to the molecule to which it is conjugated, reducing aggregation and precipitation of proteins conjugated to dPEG®24-SATA.

Hydroxylamine hydrochloride (CAS number 5470-11-1) easily removes the acetyl protecting group, exposing the sulfhydryl moiety for further reactions, for example, crosslinking to thiols or thiol-reactive groups like maleimides, bromoacetamides, and so forth. Any application that can be carried out with a traditional, non-PEGylated SATA reagent can be carried out with our SATA containing a dPEG® spacer.

Specifications

Documents

References

1. Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). References to SATA which can be directly applied to the dPEG® pegylation versions: a) general description and use, p 71; b) modification of antibodies, pp 759; c)modification of amines on nucleus and DNA probes, p. 984 and d) modification of enzymes, avidin and streptavidin with pp. 90, 909 and 919.
2. 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.
3. Silica-Shelled Single Quantum Dot Micelles as Imaging Probes with Dual or Multimodality. Rumiana Bakalova, Zhivko Zhelev, Ichio Aoki, Hideki Ohba, Yusuke Imai, and Iwao Kanno. Anal. Chem. 2006, 78 (16) pp 5925–5932. July 14, 2006. DOI: 10.1021/ac060412b