Primary pH degradation products of doramectin

Alexander F. Moore; Heather J. Lacey; Andrew Crombie; Ernest Lacey; Andrew M. Piggott

doi:10.1016/j.tetlet.2016.08.014

Primary pH degradation products of doramectin

Alexander F. Moore, Heather J. Lacey, Andrew Crombie, Ernest Lacey, Andrew M. Piggott^*

^*Corresponding author for this work

Faculty of Science and Engineering

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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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 4S epimer.

Original language	English
Pages (from-to)	4224-4227
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2016.08.014
Publication status	Published - 14 Sept 2016

Keywords

doramectin
avermectin
degradation
endectocide

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10.1016/j.tetlet.2016.08.014

Accepted author manuscriptAccepted author manuscript, 1.53 MBLicence: CC BY-NC-ND

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title = "Primary pH degradation products of doramectin",

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 Δ2,3-doramectin. The isomerisation of doramectin to Δ2,3-doramectin proceeded stereoselectively, exclusively yielding the 4S epimer.",

keywords = "doramectin, avermectin, degradation, endectocide",

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T1 - Primary pH degradation products of doramectin

AU - Moore, Alexander F.

AU - Lacey, Heather J.

AU - Crombie, Andrew

AU - Lacey, Ernest

AU - Piggott, Andrew M.

PY - 2016/9/14

Y1 - 2016/9/14

N2 - 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 Δ2,3-doramectin. The isomerisation of doramectin to Δ2,3-doramectin proceeded stereoselectively, exclusively yielding the 4S epimer.

AB - 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 Δ2,3-doramectin. The isomerisation of doramectin to Δ2,3-doramectin proceeded stereoselectively, exclusively yielding the 4S epimer.

KW - doramectin

KW - avermectin

KW - degradation

KW - endectocide

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UR - http://purl.org/au-research/grants/arc/FT130100142

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DO - 10.1016/j.tetlet.2016.08.014

M3 - Article

AN - SCOPUS:84981727363

SN - 0040-4039

VL - 57

SP - 4224

EP - 4227

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Primary pH degradation products of doramectin

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Overcoming antibiotic resistance: rapid discovery of new antibacterial drug targets using chemicalproteomics

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Primary pH degradation products of doramectin

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Overcoming antibiotic resistance: rapid discovery of new antibacterial drug targets using chemicalproteomics

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