Methods for oxime conjugation to ketone-modified polypeptides
US10172948B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Nov 24, 2014 |
| Grant date | Jan 8, 2019 |
| Priority date | — |
| Expiry date | Oct 6, 2036 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07K2317/40
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
The invention provides improved methods to prepare protein conjugates from a ketone-modified protein. In one embodiment, the protein is prepared by linking two free cysteines by reaction with a 1,3-dihaloacetone or similar ketone-containing reactant, linking the sulfur atoms of the two cysteines together. The ketone inserted between the sulfur atoms is then used to form an oxime, thus conjugating the protein to a payload. In another embodiment, two cysteine residues are tied together by reaction with a 1,3-dihaloacetone or similar reactant, and the new ketone is used to form an oxime with a suitable payload molecule, thus conjugating the protein to a payload. The method provides improved reaction conditions for the oxime formation, whereby higher yields and improved product homogeneity are achieved.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.