miun.sePublications
Change search
Refine search result
1 - 7 of 7
CiteExportLink to result list
Permanent link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Rows per page
  • 5
  • 10
  • 20
  • 50
  • 100
  • 250
Sort
  • Standard (Relevance)
  • Author A-Ö
  • Author Ö-A
  • Title A-Ö
  • Title Ö-A
  • Publication type A-Ö
  • Publication type Ö-A
  • Issued (Oldest first)
  • Issued (Newest first)
  • Created (Oldest first)
  • Created (Newest first)
  • Last updated (Oldest first)
  • Last updated (Newest first)
  • Disputation date (earliest first)
  • Disputation date (latest first)
  • Standard (Relevance)
  • Author A-Ö
  • Author Ö-A
  • Title A-Ö
  • Title Ö-A
  • Publication type A-Ö
  • Publication type Ö-A
  • Issued (Oldest first)
  • Issued (Newest first)
  • Created (Oldest first)
  • Created (Newest first)
  • Last updated (Oldest first)
  • Last updated (Newest first)
  • Disputation date (earliest first)
  • Disputation date (latest first)
Select
The maximal number of hits you can export is 250. When you want to export more records please use the Create feeds function.
  • 1.
    Hedenström, Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nguyen, Ba-Vu
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Silks III, L. A.
    Do enzymes recognise remotely located stereocentres?: Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids2002In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 13, no 8, p. 835-844Article in journal (Refereed)
    Abstract [en]

    Several racemic methyl decanoic acids have been synthesised and successfully resolved in esterification with 1-hexadecanol at aw=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids.

  • 2.
    Larsson, Michael
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nguyen, Ba-Vu
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine Sawfly Microdiprion pallipes (Hymenoptera: Diprionidae)2001In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2001, no 2, p. 353-363Article in journal (Refereed)
    Abstract [en]

    All sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis-3,4-dimethyl-gamma -butyrolactone with each of the four pure stereoisomers of 1-lithio-2,6-dimethyloctanes. The four corresponding alcohols were obtained by lipase-catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)- or (2R/S,GR)-2,6-dimethyl-1-octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11-trimethyl-2-tridecanol was also prepared.

  • 3.
    Larsson, Michael
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Ngyuen, Ba-Vu
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Synthesis and Studies of the Stereoisomeric Composition in the Sex Pheromone of Microdiprion pallipes.: Poster och abstrakt. Euchem conference, Sundsvall.1998Conference paper (Other academic)
  • 4.
    Nguyen, Ba-Vu
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Candida rugosa lipase as an enantioselective catalyst in the esterification of methyl branched carboxylic acids: Resolution of rac-3,7-dimethyl-6-octenoic acid (citronellic acid)1999In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 10, no 9, p. 1821-1826Article in journal (Refereed)
  • 5.
    Nguyen, Ba-Vu
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nordin, Ove
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Vörde, Carin
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Structure vs. Enantioselectivity in Pseudomonas cepacia Lipase Catalysed Transesterifications: Enantioselective Acylation of Primary 2-Methylalcohols1997In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 8, no 7, p. 983-986Article in journal (Refereed)
  • 6.
    Nordin, Ove
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nguyen, Ba-Vu
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Vörde, Carin
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Kinetic Resolution of Primary 2-methylalcohols via Pseudomonas cepacia Lipase Catalysed Enantioselective Acylation2000In: Journal of The Chemical Society. Perkin Transactions 1, ISSN 1472-7781, p. 367-376Article in journal (Refereed)
    Abstract [en]

    The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS, etc.) towards a series of primary 2-methyl-substituted alcohols using vinyl acetate as the acyl donor in transesterifications in organic solvents were studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 in most cases, whereas other 3-substituted primary 2-methylpropan-1-ols generally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-ols (E ≈ 20) and 2-methylalkan-1-ols (E ≈ 10). Moving the aryl group closer or further away from the chiral centre resulted in low enantioselectivities: 2-arylpropan-1-ols (E < 10), 2-methyl-4-(2-thienyl)butan-l-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-l-ol (E=3.2) and 2-methyl-6-(2-thienyl)hexan-l-ol (E=3.8).

  • 7. Östrand, Fredrik
    et al.
    Anderbrant, Olle
    Wassgren, Ann-Britt
    Bergström, Gunnar
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nguyen, Ba-Vu
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Larsson, Michael
    Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)2003In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 13, no 3, p. 155-162Article in journal (Refereed)
    Abstract [en]

    The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallen) has earlier been identified as the propionate ester of (2S,3S,7 R/S,11 R/S)/(2R,3R,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol. We now report the results from further investigations on the male response to individual stereoisomers and to blends of stereoisomers, both in electroantennographic (EAG) recordings and in field trapping experiments. We also present our attempts to determine the stereochemistry of the compounds present in females of M. pallipes. By comparing gas chromatograms and mass spectra obtained from natural extracts with those from synthetic compounds it was found that the females contain one or more of the four (2S,3S,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol isomers (SS++-1). The active pheromone component is the corresponding propionate ester 2. In EAG experiments, males responded most strongly to five propionate ester samples, namely two four-isomer blends: SS++-2 and SR++-2, and three individual stereoisomers: SSSR-, SRRR- and SRSR-2. In a series of field trapping experiments it was found that males were attracted to the SR++-2 four-isomer blend and to the individual isomer SSSR-2. Based on the EAG-recordings and field responses of males and the stereoisomers found in the females, we suggest that the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-tridecanol (SSSR-2) is used as a main component of the sex pheromone in M. pallipes. Apparently the males react to other stereoisomers in addition to that or those produced by the females.

1 - 7 of 7
CiteExportLink to result list
Permanent link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf