Unknown

Dataset Information

0

Side-chain cysteine-functionalized poly(2-oxazoline)s for multiple peptide conjugation by native chemical ligation.

ABSTRACT: We prepared statistical copolymers composed of 2-methyl-2-oxazoline (MeOx) in combination with 2-butenyl-2-oxazoline (BuOx) or 2-decenyl-2-oxazoline (DecOx) as a basis for polymer analogous introduction of 1,2-aminothiol moieties at the side chain. MeOx provides hydrophilicity as well as cyto- and hemocompatibility, whereas the alkene groups of BuOx and DecOx serve for functionalization with a thiofunctional thiazolidine by UV-mediated thiol-ene reaction. After deprotection the cysteine content in functionalized poly(2-oxazoline) (POx) is quantified by NMR and a modified trinitrobenzenesulfonic acid assay. The luminescent cell viability assay shows no negative influence of cysteine-functionalized POx (cys-POx) concerning cell viability and cell number. cys-POx was used for multiple chemically orthogonal couplings with thioester-terminated peptides through native chemical ligation (NCL), which was performed and confirmed by NMR and MALDI-ToF measurements.

SUBMITTER: Schmitz M 

PROVIDER: S-EPMC4428813 | biostudies-other | 2015 Apr

REPOSITORIES: biostudies-other

Json Xml
altmetric image

Publications

Side-chain cysteine-functionalized poly(2-oxazoline)s for multiple peptide conjugation by native chemical ligation.

Schmitz Michael M   Kuhlmann Matthias M   Reimann Oliver O   Hackenberger Christian P R CP   Groll Jürgen J  

Biomacromolecules 20150320 4

We prepared statistical copolymers composed of 2-methyl-2-oxazoline (MeOx) in combination with 2-butenyl-2-oxazoline (BuOx) or 2-decenyl-2-oxazoline (DecOx) as a basis for polymer analogous introduction of 1,2-aminothiol moieties at the side chain. MeOx provides hydrophilicity as well as cyto- and hemocompatibility, whereas the alkene groups of BuOx and DecOx serve for functionalization with a thiofunctional thiazolidine by UV-mediated thiol-ene reaction. After deprotection the cysteine content  ...[more]

Similar Datasets

Unknown Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides.
| S-EPMC5320936 | biostudies-literature
Unknown Enabling Cysteine-Free Native Chemical Ligation at Challenging Junctions with a Ligation Auxiliary Capable of Base Catalysis.
| S-EPMC8457107 | biostudies-literature
Unknown Peptide Conjugation to a Polymer Coating via Native Chemical Ligation of Azlactones for Cell Culture.
| S-EPMC5172394 | biostudies-literature
Unknown Efficient Synthesis of Peptide and Protein Functionalized Pyrrole-Imidazole Polyamides Using Native Chemical Ligation.
| S-EPMC4490465 | biostudies-literature
Unknown Thermoresponsive Molecular Brushes with a Rigid-Chain Aromatic Polyester Backbone and Poly-2-alkyl-2-oxazoline Side Chains.
| S-EPMC8622345 | biostudies-literature
Unknown Thionoesters: A Native Chemical Ligation-Inspired Approach to Cysteine-Triggered H<sub>2</sub>S Donors.
| S-EPMC6504978 | biostudies-literature
Unknown Hydrogels cross-linked by native chemical ligation.
| S-EPMC2790863 | biostudies-literature
Unknown Site-Specific Three-Color Labeling of ?-Synuclein via Conjugation to Uniquely Reactive Cysteines during Assembly by Native Chemical Ligation.
| S-EPMC6014907 | biostudies-literature
Unknown Alendronate-Functionalized Poly(2-oxazoline)s with Tunable Affinity for Calcium Cations.
| S-EPMC6692821 | biostudies-literature
Unknown In situ vesicle formation by native chemical ligation.
| S-EPMC4418804 | biostudies-literature