Primary pH degradation products of doramectin. Issue 37 (14th September 2016)

• Record Type: Journal Article
• Authors: Moore, Alexander F.; Lacey, Heather J.; Crombie, Andrew; Lacey, Ernest; Piggott, Andrew M.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 37(2016)
• Page Start: 4224
• Page End: 4227
• Publication Date: 2016-09-14
• Subjects: Doramectin -- Avermectin -- Degradation -- Endectocide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.014
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Primary pH degradation products of the antiparasitic drug doramectin are reported. Preparation and characterisation of acid and base degradation products of doramectin. Definitive reference standards for trace analysis of food and soil samples. Abstract: Herein, we report the preparation and characterisation of the primary pH degradation products of doramectin, a potent second-generation endectocide. Under mildly acidic conditions, doramectin underwent sequential deglycosylation to yield doramectin monosaccharide and doramectin aglycone respectively. Under basic conditions, doramectin isomerised reversibly to give 2-epidoramectin and irreversibly to give Δ 2, 3 -doramectin. The isomerisation of doramectin to Δ 2, 3 -doramectin proceeded stereoselectively, exclusively yielding the 4 S epimer.