Histidine protection

US4591648A · kind A · utility

Assignee

• NATIONAL RESEARCH DEVELOPMENT CORPORATION · GB

Inventors

• John H. Jones · Seattle, US
• Tom Brown · West Chester, US

Key dates

• Filing date: Mar 24, 1982
• Grant date: May 27, 1986
• Expiry date: Mar 24, 2002

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

Histidine derivatives of formula I are useful inter alia in peptide synthesis. ##STR1## wherein: X represents --CH.sub.2 OCH.sub.2 Ar, in which Ar is a phenyl substituent optionally substituted by one or more halogen, alkoxy, alkyl or nitro groups; PA1 Y, which differs from X, represents hydrogen, a protective group capable of inhibiting self coupling during formation of a peptide bond, an amino acid residue, a peptide chain or an antibiotic residue; PA1 E represents OH,OM,M representing an alkali metal or ammonium, OR, R representing an alkyl, aryl, aralkyl or alkaryl group, an amino acid residue, a peptide chain or an antibiotic residue; the compound I being optionally in the form of a hydrate or acid salt. In compounds I of especial interest, X represents benzyloxymethyl or p-bromobenzyloxymethyl, Y represents t-butyloxycarbonyl and E represents --OH.