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902578

Sigma-Aldrich

Hydroxy-PEG6-t-butyl ester

≥95%

Synonym(s):

tert-Butyl 1-hydroxy-3,6,9,12,15,18-hexaoxahenicosan-21-oate, HO-PEG6-CO-OtBu

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About This Item

Empirical Formula (Hill Notation):
C19H38O9
CAS Number:
361189-64-2
Molecular Weight:
410.50
UNSPSC Code:
51171641
NACRES:
NA.22

assay

≥95%

form

liquid

reaction suitability

reagent type: cross-linking reagent

refractive index

n/D 1.454

density

1.068

functional group

ester
hydroxyl

storage temp.

−20°C

SMILES string

O=C(OC(C)(C)C)CCOCCOCCOCCOCCOCCOCCO

InChI

1S/C19H38O9/c1-19(2,3)28-18(21)4-6-22-8-10-24-12-14-26-16-17-27-15-13-25-11-9-23-7-5-20/h20H,4-17H2,1-3H3

InChI key

VGGDPFAYSOSIOK-UHFFFAOYSA-N

Related Categories

Application

This heterobifunctional, PEGylated crosslinker features a hydroxyl group at one end and t-butyl-protected carboxylic acid at the other, which can be deprotected with acidic conditions. The hydrophillic PEG linker facilitates solubility in biological applications. Hydroxy-PEG6-t-butyl ester can be used for bioconjugation or as a building block for synthesis of small molecules, conjugates of small molecules and/or biomolecules, or other tool compounds for chemical biology and medicinal chemistry that require ligation. Examples of applications include its synthetic incorporation into antibody-drug conjugates or roteolysis-targeting chimeras (PROTAC® molecules) for targeted protein degradation.

Other Notes

Synthesis and Molecular Recognition Studies of the HNK-1 Trisaccharide and Related Oligosaccharides. The Specificity of Monoclonal Anti-HNK-1 Antibodies as Assessed by Surface Plasmon Resonance and STD NMR

Maleimide-oligo(ethylene glycol) Derivatives of Camptothecin as Albumin-Binding Prodrugs: Synthesis and Antitumor Efficacy

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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wgk_germany

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flash_point_f

Not applicable

flash_point_c

Not applicable

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André Warnecke et al.
Bioconjugate chemistry, 14(2), 377-387 (2003-03-20)
In situ binding of thiol-reactive prodrugs to the cysteine-34 position of circulating albumin is a new approach in drug delivery. Therefore, five maleimide-bearing derivatives of the anticancer drug camptothecin (CPT) were developed as albumin-binding prodrugs. These compounds were synthesized by
Yury E Tsvetkov et al.
Journal of the American Chemical Society, 134(1), 426-435 (2011-11-18)
The human natural killer cell carbohydrate, HNK-1, plays function-conducive roles in peripheral nerve regeneration and synaptic plasticity. It is also the target of autoantibodies in polyneuropathies. It is thus important to synthesize structurally related HNK-1 carbohydrates for optimizing its function-conducive

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