Transesterification and other conversion reactions of acid derivatives, using an amidine base

US6090913A · kind A · utility

Assignee

• Degussa-Huels AG · DE

Inventors

• Karlheinz Drauz · Alzenau, DE
• Thomas Muller · Bad Homburg vor der Höhe, DE
• Matthias Kottenhahn · Alzenau, DE
• Dieter Seebach · Zürich, CH
• Adrian Thaler · Steinhausen, CH

Key dates

• Filing date: Mar 27, 1997
• Grant date: Jul 18, 2000
• Expiry date: Mar 27, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07K1/126
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

A process employs amidine or amidine base and a metal compound in the presence of an alcohol or water to transesterify, or saponify esters or amides. Since the process employs relatively mild conditions, it is especially suitable for the production of optically active substances and biomolecules, e.g. peptides, amino acids and nucleic acids which are sensitive to elevated temperatures, extreme pH values and/or long reaction times since these compounds are easily racemised or denatured. The conditions additionally find use in solid phase systems. When amino acid or peptide esters are saponified, the splitting is brought about with lithium hydroxide alone under mild conditions. The use of an amidine base, more particularly DBU or DBN, in combination with the metal salt additionally accelerates the reaction so strongly that even sensitive acid derivatives can be reacted under mild conditions. The amidine based system lends itself to the manufacture of complex esters, gentle splitting of peptides from the carrier, gentle saponification of amides or esters.