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Kiral kirleticiler ve çevresel önemi

Yıl 2016, Cilt: 22 Sayı: 6, 486 - 496, 20.12.2016

Öz

Kiralite,
canlı sistemlerden doğal ve sentetik organik maddelere kadar hayatımızın birçok
alanında bulunmaktadır. En genel ifadeyle ayna görüntüsü kendisiyle çakışmayan
maddeler olarak tanımlanan kiral moleküller, başta ilaç sanayi ve tıp olmak
üzere birçok alanda kullanılmaktadır. Söz konusu maddelere ait ayna
görüntülerinden her biri enantiyomer olarak adlandırılır ve kiral maddelere ait
enantiyomerlerden biri kullanım amacına uygun hareket ederken diğeri veya her
ikisi de çevresel ortamlarda kirliliğe ve canlılarda toksik etkiye neden
olabilmektedir. Enantiyomerlerin yalnızca biyolojik değişime uğrama
potansiyelleri farklılık göstermekte, bu özelliği sebebiyle kiral kirleticiler,
güncel kirliliğin değerlendirilmesi amacıyla çevresel kirlilik araştırmalarına
konu olmaktadır. Toprak, sediman, hava ve su ortamının yanı sıra canlılarda da,
başta kromatografik yöntemler olmak üzere çeşitli metotlarla tespit
edilebilmektedir. Bu derlemede, kiralite ve çevresel açıdan önem arz eden kiral
bileşiklerin özellikleri, analiz yöntemleri ve çevredeki akıbetleri
değerlendirilmiştir. Çeşitli avantajları nedeniyle endüstriyel uygulamalarda
geniş yer bulan kiral bileşiklerden kullanım amacının dışında çevreye salınan
bileşikler, biyolojik aktiviteleri nedeniyle çevresel izleme çalışmalarında
önem arz etmektedir. Ülkemizde çevresel ortamlarda henüz araştırmalara konu
olmaya başlayan kiral kirleticilerin akıbetinin değerlendirilmesi açısından
enantiyoseçici davranışlarının anlaşılması önem arz etmektedir.

Kaynakça

  • Ali I, Aboul-Enein HY. Chiral Pollutants: Distribution, Toxicity and Analysis by Chromatography and Capillary Electrophoresis. Chichester, England, Wiley, 2004.
  • Müller TA, Kohler HPE. "Chirality of pollutants-effects on metabolism and fate". Applied Microbiology and Biotechnology, 64(3), 300-316, 2004.
  • Ali I, Gupta VK, Aboul-Enein HY. "Chirality: A challenge for the environmental scientists". Current Science, 84(2), 152-156, 2003.
  • Wiberg K. Enantiospecific Analysis and Environmental Behavior of Chiral Persistent Organic Pollutants (POPs). PhD Thesis, Umea University, Umea, Sweden, 2002.
  • Kallenborn R, Hühnerfuss H. Chiral Environmental Pollutants: Trace Analysis and Ecotoxicology, Berlin, Deutschland, Springer, 2001.
  • Ulrich EM, Morrison CN, Goldsmith MR, Foreman WT. "Chiral Pesticides: Identification, Description, and Environmental Implications". Reviews of Environmental Contamination and Toxicology, 217, 1-74, 2012.
  • Mislow KM. Introduction to Stereochemistry. 1st ed. Mineola, ABD, Courier Dover Publications, 1965.
  • Eliel EL, Wilen SH. Stereochemistry of Organic Compounds. 1st ed. USA, Wiley-Intersscience, 1994.
  • Venier M, Hites RA. "Chiral organochlorine pesticides in the atmosphere". Atmospheric Environment, 41(4), 768-775, 2007.
  • Wong CS, Hoestra PF, Karlsson H, Backus SM, Mabury SA, Muir DCG. "Enantiomer fractions of chiral organochlorine pesticides and polychlorinated biphenyls in standard and certified reference materials". Chemosphere, 49(10), 1339-1347, 2002.
  • Xie J, Duan Y, Che S. "Chirality of metal nanoparticles in chiral mesoporous silica". Advanced Functional Materials, 22(18), 3784-3792, 2012.
  • Fan Z, Govorov AO. "Plasmonic circular dichroism of chiral metal nanoparticle assemblies". Nano Letters, 10(7), 2580-2587, 2010.
  • Eljarrat E, Guerra P, Barcelo D. "Enantiomeric determination of chiral persistent organic pollutants and their metabolites". Trends in Analytical Chemistry, 27(10), 847-861, 2008.
  • Zipper C, Bolliger C, Fleischmann T, Suter MJF, Angst W, Müller MD, Kohler HPE. "Fate of the herbicides mecoprop, dichlorprop and 2, 4-D in aerobic and anaerobic sewage sludge as determined by laboratory batch studies and enantiomer-specific analysis". Biodegradation, 10(4), 271-278, 1999.
  • Nejem RM. Enantioselective Sensors and Biosensors for Clinical Analysis. PhD Thesis, University of Pretoria, Pretoria, South Africa, 2004.
  • Nguyen LA, He H, Pham-Huy C. "Chiral drugs: An overview". International Journal of Biomedical Science, 2(2), 85-100, 2006.
  • Evans SE, Kasprzyk-Hordern B. "Applications of chiral chromatography coupled with mass spectrometry in the analysis of chiral pharmaceuticals in the environment". Trends in Environmental Analytical Chemistry, 1, 34-51, 2014.
  • Kasprzyk-Hordern B. "Pharmacologically active compounds in the environment and their chirality". Chemical Society Reviews, 39(11), 4466-4503, 2010.
  • Ong AL, Kamaruddin AH, Bhatia S, Long WS, Lim ST, Kumari R. "Performance of free candida antarctica lipase b in the enantioselective esterification of (R)-ketoprofen". Enzyme and Microbial Technology, 39(4), 924-929, 2006.
  • Sheldon RA. "Chirotechnology: Designing economic chiral syntheses". Journal of Chemical Technology & Biotechnology, 67(1), 1-14, 1996.
  • Lewis DL, Garrison AW, Wommack KE, Whittemore A, Steudler P, Melillo J. "Influence of environmental changes on degradation of chiral pollutants in soils". Nature, 401(6756), 898-901, 1999.
  • Buerge IJ, Bächli A, Heller WE, Keller M, Poiger T. "Environmental behavior of the chiral herbicide haloxyfop. 2. unchanged enantiomer composition in blackgrass (Alopecurus myosuroides) and garden cress (Lepidium sativum)". Journal of Agricultural and Food Chemistry, 63(10), 2591-2596, 2015.
  • Hühnerfuss H, Faller J, Koenig WA, Ludwig P. "Gas chromatographic separation of the enantiomers of marine pollutants. 4. fate of hexachlorocyclohexane ısomers in the baltic and north sea". Environmental Science & Technology, 26(11), 2127-2133, 1992.
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Chiral pollutants and their significance in the environment

Yıl 2016, Cilt: 22 Sayı: 6, 486 - 496, 20.12.2016

Öz

Chirality
exists in a wide range of objects in the universe from living creatures to
natural or synthetic organic materials. As a common expression, any objects
that are not superimposable on its mirror image are described as chiral
molecules, and such materials are used in various fields including
pharmaceutical industry and medicine. Each mirror image of chiral molecules are
called enantiomer and while one of the enantiomers may be active and more toxic
than the other in its application area and once they enter to the environmental
compartments less-active enantiomer or both enantiomers can cause environmental
pollution and toxicity on living organisms. Enantiomers show difference in
biological degradation such that this property is used as a useful tool in
environmental pollution assessment/research studies. In addition to the
environmental compartments such as soil, sediment, air and water, they are also
analyzed in living organisms by various methods including primarily the
chromatographic methods. In this review, chirality and the properties, analysis
methods and fate of the chiral chemicals which have significance in the
environmental studies are presented. Due to various advantages, chiral
chemicals are used in several industrial products and once they are released to
the environment, they become environmentally concerned pollutants and play an
important role in environmental monitoring studies due to their biological
activities. In our country, although it is very limited, chiral pollutants have
already became subject to monitoring studies, hence, understanding the
enantioselective degradation of such chemicals in different environmental
compartments is important to assess the fate of these chemicals.

Kaynakça

  • Ali I, Aboul-Enein HY. Chiral Pollutants: Distribution, Toxicity and Analysis by Chromatography and Capillary Electrophoresis. Chichester, England, Wiley, 2004.
  • Müller TA, Kohler HPE. "Chirality of pollutants-effects on metabolism and fate". Applied Microbiology and Biotechnology, 64(3), 300-316, 2004.
  • Ali I, Gupta VK, Aboul-Enein HY. "Chirality: A challenge for the environmental scientists". Current Science, 84(2), 152-156, 2003.
  • Wiberg K. Enantiospecific Analysis and Environmental Behavior of Chiral Persistent Organic Pollutants (POPs). PhD Thesis, Umea University, Umea, Sweden, 2002.
  • Kallenborn R, Hühnerfuss H. Chiral Environmental Pollutants: Trace Analysis and Ecotoxicology, Berlin, Deutschland, Springer, 2001.
  • Ulrich EM, Morrison CN, Goldsmith MR, Foreman WT. "Chiral Pesticides: Identification, Description, and Environmental Implications". Reviews of Environmental Contamination and Toxicology, 217, 1-74, 2012.
  • Mislow KM. Introduction to Stereochemistry. 1st ed. Mineola, ABD, Courier Dover Publications, 1965.
  • Eliel EL, Wilen SH. Stereochemistry of Organic Compounds. 1st ed. USA, Wiley-Intersscience, 1994.
  • Venier M, Hites RA. "Chiral organochlorine pesticides in the atmosphere". Atmospheric Environment, 41(4), 768-775, 2007.
  • Wong CS, Hoestra PF, Karlsson H, Backus SM, Mabury SA, Muir DCG. "Enantiomer fractions of chiral organochlorine pesticides and polychlorinated biphenyls in standard and certified reference materials". Chemosphere, 49(10), 1339-1347, 2002.
  • Xie J, Duan Y, Che S. "Chirality of metal nanoparticles in chiral mesoporous silica". Advanced Functional Materials, 22(18), 3784-3792, 2012.
  • Fan Z, Govorov AO. "Plasmonic circular dichroism of chiral metal nanoparticle assemblies". Nano Letters, 10(7), 2580-2587, 2010.
  • Eljarrat E, Guerra P, Barcelo D. "Enantiomeric determination of chiral persistent organic pollutants and their metabolites". Trends in Analytical Chemistry, 27(10), 847-861, 2008.
  • Zipper C, Bolliger C, Fleischmann T, Suter MJF, Angst W, Müller MD, Kohler HPE. "Fate of the herbicides mecoprop, dichlorprop and 2, 4-D in aerobic and anaerobic sewage sludge as determined by laboratory batch studies and enantiomer-specific analysis". Biodegradation, 10(4), 271-278, 1999.
  • Nejem RM. Enantioselective Sensors and Biosensors for Clinical Analysis. PhD Thesis, University of Pretoria, Pretoria, South Africa, 2004.
  • Nguyen LA, He H, Pham-Huy C. "Chiral drugs: An overview". International Journal of Biomedical Science, 2(2), 85-100, 2006.
  • Evans SE, Kasprzyk-Hordern B. "Applications of chiral chromatography coupled with mass spectrometry in the analysis of chiral pharmaceuticals in the environment". Trends in Environmental Analytical Chemistry, 1, 34-51, 2014.
  • Kasprzyk-Hordern B. "Pharmacologically active compounds in the environment and their chirality". Chemical Society Reviews, 39(11), 4466-4503, 2010.
  • Ong AL, Kamaruddin AH, Bhatia S, Long WS, Lim ST, Kumari R. "Performance of free candida antarctica lipase b in the enantioselective esterification of (R)-ketoprofen". Enzyme and Microbial Technology, 39(4), 924-929, 2006.
  • Sheldon RA. "Chirotechnology: Designing economic chiral syntheses". Journal of Chemical Technology & Biotechnology, 67(1), 1-14, 1996.
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  • Aigner EJ, Leone AD, Falconer RL. "Concentrations and enantiomeric ratios of organochlorine pesticides in soils from the US corn belt". Environmental Science & Technology, 32(9), 1162-1168, 1998.
  • Wiberg K, Harner T, Wideman JL, Bidleman TF. "Chiral analysis of organochlorine pesticides in alabama soils". Chemosphere, 45(6), 843-848, 2001.
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  • Ludwig P, Huhnerfuss H, Konig WA, Gunkel W. "Gas-Chromatographic separation of the enantiomers of marine pollutants. 3. enantioselective degradation of alpha-hexachlorocyclohexane and gamma-hexachlorocyclohexane by marine microorganisms". Marine Chemistry, 38(1-2), 13-23, 1992.
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Toplam 102 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik
Bölüm Derleme
Yazarlar

Emine Can Güven

Dilek Bolat Bu kişi benim

Kadir Gedik

Perihan Binnur Kurt Karakuş

Yayımlanma Tarihi 20 Aralık 2016
Yayımlandığı Sayı Yıl 2016 Cilt: 22 Sayı: 6

Kaynak Göster

APA Can Güven, E., Bolat, D., Gedik, K., Kurt Karakuş, P. B. (2016). Kiral kirleticiler ve çevresel önemi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, 22(6), 486-496.
AMA Can Güven E, Bolat D, Gedik K, Kurt Karakuş PB. Kiral kirleticiler ve çevresel önemi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. Aralık 2016;22(6):486-496.
Chicago Can Güven, Emine, Dilek Bolat, Kadir Gedik, ve Perihan Binnur Kurt Karakuş. “Kiral Kirleticiler Ve çevresel önemi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 22, sy. 6 (Aralık 2016): 486-96.
EndNote Can Güven E, Bolat D, Gedik K, Kurt Karakuş PB (01 Aralık 2016) Kiral kirleticiler ve çevresel önemi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 22 6 486–496.
IEEE E. Can Güven, D. Bolat, K. Gedik, ve P. B. Kurt Karakuş, “Kiral kirleticiler ve çevresel önemi”, Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, c. 22, sy. 6, ss. 486–496, 2016.
ISNAD Can Güven, Emine vd. “Kiral Kirleticiler Ve çevresel önemi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 22/6 (Aralık 2016), 486-496.
JAMA Can Güven E, Bolat D, Gedik K, Kurt Karakuş PB. Kiral kirleticiler ve çevresel önemi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2016;22:486–496.
MLA Can Güven, Emine vd. “Kiral Kirleticiler Ve çevresel önemi”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, c. 22, sy. 6, 2016, ss. 486-9.
Vancouver Can Güven E, Bolat D, Gedik K, Kurt Karakuş PB. Kiral kirleticiler ve çevresel önemi. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2016;22(6):486-9.





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