Synthesis of N-substituted peptide amides
US4701499A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Feb 3, 1986 |
| Grant date | Oct 20, 1987 |
| Priority date | — |
| Expiry date | Feb 3, 2006 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY10S930/28
- WIPO fieldBiotechnology
- WIPO sectorChemistry
Abstract
Peptide N-alkylamides, and other C-terminal N-substituted amides, can be synthesized using solid-phase synthesis on a benzene-containing resin which is suitably methylated. Reactive amino groups are attached directly or indirectly to the methyl groups, for example, such as by reacting commercially available chloromethylated polystyrene resins with an alkylamine to create a resin-amine. The C-terminal amino acid of the desired peptide is linked to the resin-amine via an amide linkage, and the peptide is thereafter built in normal fashion. Treatment of the completed peptide intermediate with HF is effective to both effect deprotection and cleave the peptide from the resin in the form of the N-substituted amide. Examples include peptide N-ethylamides, N-fluoroethylamide, N-anilides and other substituted N-benzylamides.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.