Metal-ligating amino acid derivatives for MRI and for peptide synthesis

US5637759A · kind A · utility

Assignee

• The Regents of the University of California · US

Inventors

• John E. Hearst · Berkeley, US
• Tariq M. Rana · San Diego, US
• Matt Ban · San Francisco, US

Key dates

• Filing date: Jul 30, 1992
• Grant date: Jun 10, 1997
• Expiry date: Jul 30, 2012

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/18
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Novel organic compounds and metal ion-containing amino acid chelates are described which are useful in solid phase synthesis of polypeptides and as magnetic resonance imaging (MRI) enhancing agents. The present invention also relates to a convenient and straightforward method to synthesize a metal-ligating amino acid suitable as MRI enhancing agents or for introducing a strong metal binding site at any chosen position in a peptide. Some compounds are designed to be compatible with N-.alpha.-Fmoc peptide synthesis strategy, and can easily be prepared on large scale. Thus, flexible linkers of different lengths and containing various structures can be placed between the .alpha.-carbon backbone of peptides and metal binding moieties. These peptides will provide a variety of affinity cleaving reagents which can be directed against protein or nucleic acid targets. Therefore, these molecules can serve as an important tool to study protein folding, protein-protein and protein-nucleic acid interactions.