Synthesis of N-substituted peptide amides

Details Synthesis of N-substituted peptide amides Synthesis of N-substituted peptide amides

1986-02-03

1987-10-20

Kight, John

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

5253334, 5253336, 525 5411, C08F 818, C08F 1208, C08F11208, C08F21208

Patent

active

047014997

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.

REFERENCES:
patent: 4569967 (1986-02-01), Kornreich et al.

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