Back to results
US 12,540,162 B2Granted
Preparation of functional homocysteine residues in polypeptides and peptides
AssigneeThe Regents of the University of California
InventorsTimothy J. Deming, Eric G. Gharakhanian
Life of this patent
Estimating the term…
Abstract
Methodology was developed for transformation of methionine residues into homocysteine derivatives. Methionine residues can undergo alkylation reactions at low pH to yield sulfonium ions, which can then be selectively demethylated to give alkyl homocysteine residues. This process tolerates many functional groups.
Claims22
A method of preparing a polypeptide comprising one or more RCH residues, wherein each R—CH residue in the polypeptide has a structure represented by formula (I):
- wherein:
- RX, independently for each —CH residue, is H or alkyl;
- and R, independently for each R—CH residue, is substituted or unsubstituted alkyl, provided that R is not unsubstituted methyl, allyl, benzyl, oligoethylene glycol, or glycosylated alkyl, and further provided that R does not contain sulfoxide;
- comprising contacting an MR sulfonium residue represented by formula (II) with a resonance stabilized anionic nucleophile, in the presence of an organic solvent that is miscible with water, thereby demethylating the MR sulfonium residue and forming the polypeptide comprising one or more R—CH residues, wherein each R—CH residue in the polypeptide has a structure represented by formula (I) and wherein MR has a structure represented by formula (II):
- and
- further wherein R is less electrophilic and more sterically demanding relative to the methyl group of formula II.
3 more elements
Dependencies are inferred from the claim text.