Patent ID: 6380358
Filing Date: 2002-04-30
Classification: C07C,C07K,Y02P

Abstract:
A method for solid phase synthesis of a peptide comprising one or more arginine homologs, comprising the steps of:(a) assembling a sequence (Xaa)n of amino acids on a solid phase peptide synthesis resin, where Xaa denotes any appropriately protected amino acid and n denotes an integer; (b) attaching an amino acid having the structure wherein Q is Boc or Fmoc and P is any protecting group that can be selectively removed, and n=0-3, to the amino terminus of the product of step (a);(c) coupling any sequence of suitably protected amino acids to the amino terminus of the product of step (b); (d) selectively removing all the protecting groups P as defined in (b) from the product of step (c); (e) reacting a protected guanidine having the structure wherein P1 and P2 are the same or different urethane protecting groups, and R is a substituted or unsubstituted alkyl or aryl group or a heterocyclic group, with the product of step (d) to guanidinylate all unprotected amino functions present; and(f) removing all protecting groups and cleaving the peptide from the resin to yield the product wherein m denotes an integer.