The use of immobilized enzymes in organic synthesis. Part 6. Oxidation of 1-alkyl-3-carbamoylpyridinium chlorides by rabbit liver aldehyde oxidase

✍ Scribed by S. A. G. F. Angelino; D. J. Buurman; H. C. van der Plas; F. Müller

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 555 KB
• Volume: 101
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19821011005

✦ Synopsis

Abstract

A method is described for the oxidation of some 1‐alkyl‐3‐carbamoylpyridinium chlorides by reaction with immobilized rabbit liver aldehyde oxidase. With the 1‐methyl‐, 1‐ethyl‐and 1‐n‐propyl derivatives, only the 1‐alkyl‐1,6‐dihydro‐6‐oxo‐3‐pyridinecarboxamides have been obtained, but with the t‐Bu analogue the corresponding 4‐oxo compound was found as single product. The i‐Pr derivative gave rise to a mixture of the corresponding 4‐ and 6‐oxo compounds. From the kinetic data some information has been acquired with respect to the enzyme active‐site environment and the binding of the substrates to the enzyme.