Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species
Author
Summary, in English
Abstract in Undetermined
Stereoisomers of long-chain secondary alcohols are used as sex pheromone precursors among pine sawflies and some species can be severe pine forest pests. To use their pheromone in environmentally friendly pest management, methods are needed that can determine the stereochemistry of the precursor alcohols. Combinations of 11 acid chloride derivatives and 10 GC columns were evaluated for separation of stereoisomers of 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol, and 3,7-dimethylpentadecan-2-ol. Derivatization with (S)-2-acetoxypropionyl chloride in combination with a Chiraldex B-PA column separated all eight stereoisomers of 3,7dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol. A combination of two different derivatization methods was needed to separate all stereoisomers of the longer chained alcohols 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol. A female extract of the pine sawfly Neodiprion lecontei was also analyzed and the stereochemistry of the sex pheromone alcohol precursor was determined to be (2S,3S,7S)-3,7-dimethylpentadecan-2-ol at an amount of about 7 ng/female. This paper presents the first GC-MS separation of all eight stereoisomers of 3,7-dimethylundecan-2-ol, 3,7dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol in a single analytical run and also the first GC-MS determination of the stereochemistry of the sex pheromone precursor found in females of N. lecontei.
Stereoisomers of long-chain secondary alcohols are used as sex pheromone precursors among pine sawflies and some species can be severe pine forest pests. To use their pheromone in environmentally friendly pest management, methods are needed that can determine the stereochemistry of the precursor alcohols. Combinations of 11 acid chloride derivatives and 10 GC columns were evaluated for separation of stereoisomers of 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol, and 3,7-dimethylpentadecan-2-ol. Derivatization with (S)-2-acetoxypropionyl chloride in combination with a Chiraldex B-PA column separated all eight stereoisomers of 3,7dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol. A combination of two different derivatization methods was needed to separate all stereoisomers of the longer chained alcohols 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol. A female extract of the pine sawfly Neodiprion lecontei was also analyzed and the stereochemistry of the sex pheromone alcohol precursor was determined to be (2S,3S,7S)-3,7-dimethylpentadecan-2-ol at an amount of about 7 ng/female. This paper presents the first GC-MS separation of all eight stereoisomers of 3,7-dimethylundecan-2-ol, 3,7dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol in a single analytical run and also the first GC-MS determination of the stereochemistry of the sex pheromone precursor found in females of N. lecontei.
Department/s
Publishing year
2012
Language
English
Pages
1016-1027
Publication/Series
Analytical Letters
Volume
45
Issue
9
Document type
Journal article
Publisher
Taylor & Francis
Topic
- Biological Sciences
- Zoology
Keywords
- alcohols
- Secondary
- Pine sawflies
- Neodiprion lecontei
- Derivatization
- GC-MS
- Sex pheromone
- Stereoisomers
Status
Published
Project
- Chemical communication in sawflies
Research group
- Pheromone Group
ISBN/ISSN/Other
- ISSN: 0003-2719