Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species
(2012) In Analytical Letters 45(9). p.1016-1027- Abstract
- 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,... (More) - 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. (Less)
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https://lup.lub.lu.se/record/2863091
- author
- Bång, Joakim ; Hedenström, Erik and Anderbrant, Olle LU
- organization
- publishing date
- 2012
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- alcohols, Secondary, Pine sawflies, Neodiprion lecontei, Derivatization, GC-MS, Sex pheromone, Stereoisomers
- in
- Analytical Letters
- volume
- 45
- issue
- 9
- pages
- 1016 - 1027
- publisher
- Taylor & Francis
- external identifiers
-
- wos:000305209100007
- scopus:84862506238
- ISSN
- 0003-2719
- DOI
- 10.1080/00032719.2012.670789
- project
- Chemical communication in sawflies
- language
- English
- LU publication?
- yes
- id
- 93ae41b0-2ccb-4f99-884c-2f303a3fe1f3 (old id 2863091)
- date added to LUP
- 2016-04-01 14:41:55
- date last changed
- 2024-01-10 07:26:57
@article{93ae41b0-2ccb-4f99-884c-2f303a3fe1f3,
abstract = {{Abstract in Undetermined<br/>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.}},
author = {{Bång, Joakim and Hedenström, Erik and Anderbrant, Olle}},
issn = {{0003-2719}},
keywords = {{alcohols; Secondary; Pine sawflies; Neodiprion lecontei; Derivatization; GC-MS; Sex pheromone; Stereoisomers}},
language = {{eng}},
number = {{9}},
pages = {{1016--1027}},
publisher = {{Taylor & Francis}},
series = {{Analytical Letters}},
title = {{Stereoisomeric separation of derivatised 2-alkanols using gas chromatography – mass spectrometry: sex pheromone precursors found in pine sawfly species}},
url = {{http://dx.doi.org/10.1080/00032719.2012.670789}},
doi = {{10.1080/00032719.2012.670789}},
volume = {{45}},
year = {{2012}},
}