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US 2007/0179279 A1Published application
Methods for the synthesis of arginine-containing peptides
OwnerLin Chen, Christopher Robertsinventors
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Abstract
Methods for the synthesis of arginine-containing peptides are provided. The methods include a step that minimizes contact of side chain protected arginine with base prior to the coupling step.
Claims26
A method of adding arginine to a nascent peptide comprising steps of:
- obtaining an inactive coupling composition comprising dissolved side chain unprotected arginine comprising an acid-removable alpha amino protecting group, and
- coupling the side chain unprotected arginine to a nascent peptide in the presence of an active coupling composition, wherein the nascent peptide comprises a tryptophan residue, or the method further comprises a step of coupling a tryptophan residue to the nascent peptide comprising the side chain unprotected arginine.
A method of preparing an arginine—and tryptophan-containing peptide comprising steps of:
- coupling tryptophan comprising an acid-removable alpha amino protecting group to a nascent peptide to provide a tryptophan-containing nascent peptide,
- preparing an inactive coupling composition comprising dissolved side chain unprotected arginine comprising an acid-removable alpha amino protecting group, and
- coupling the side chain unprotected arginine to the tryptophan-containing nascent peptide comprising a tryptophan residue in the presence of an active coupling composition.
A method of preparing a peptide having a sequence:
- AAnn-(D)Phe-Arg-Trp-Gly-NH2 (SEQ ID NO:1), wherein AAnn represents a non-natural amino acid comprising a step of coupling a side chain unprotected arginine comprising an acid-removable alpha amino protecting group to a nascent peptide having the sequence Trp-Gly-R, wherein R represents resin.
Dependencies are inferred from the claim text.