Radioracemization and radiation-induced chiral amplification of chiral terpenes measured by optical rotatory dispersion (ORD) spectroscopy

作者: Franco Cataldo , Ornella Ursini , Giancarlo Angelini

DOI: 10.1016/J.RADPHYSCHEM.2008.03.003

关键词: Chirality (chemistry)IrradiationOptical rotatory dispersionSpectroscopyRadiolysisOptical rotationStereochemistryPineneChemistryEnantiomeric excessAnalytical chemistry

摘要: Abstract For the first time radioracemization of α (+)pinene and (−)pinene, turpentine R (−)- -phellandrene has been studied by optical rotatory dispersion (ORD) spectroscopy. all these compounds, implies a shift ORD curves toward lower levels specific rotation. The degree ( ) defined calculated for compounds studied. It found that radiation dose 1 MGy is about 4.5% compound with highest purity reaches 7–8% less optically pure demonstrating impurities can affect greatly radioracemization. In contrast general effect exerted high-energy on chiral molecules, β when irradiated show an increment their This fact measured spectroscopy amplification chirality reach 1000% in near UV. phenomenon due to formation polymer, poly- -pinene, which forms solution monomer enhancing its activity. implications theories origin life such unexpected are discussed briefly.

参考文章(37)
Koji Nakanishi, Infrared Absorption Spectroscopy ,(1977)
Ryoichi Hayatsu, Edward Anders, Organic compounds in meteorites and their origins coge. ,vol. 99, pp. 1- 37 ,(1981) , 10.1007/3-540-10920-X_13
M. A. El-Ries, M. M. Abou Sekkina, Thermal Stability of γ-irradiated Tolbutamide Journal of Thermal Analysis and Calorimetry. ,vol. 55, pp. 291- 300 ,(1999) , 10.1023/A:1010129415876
B. Marciniec, M. Kozak, L. Wachowski, M. Ogrodowczyk, Evaluation of radiostability of some steroid derivatives Journal of Thermal Analysis and Calorimetry. ,vol. 73, pp. 473- 485 ,(2003) , 10.1023/A:1025465726691
William A. Bonner, Hillary Hall, George Chow, Yi Liang, Richard M. Lemmon, The radiolysis and radioracemization of amino acids on clays. Origins of Life and Evolution of Biospheres. ,vol. 15, pp. 103- 114 ,(1985) , 10.1007/BF01809492
William A. Bonner, Experimental evidence for ?-decay as a source of chirality by enantiomer analysis Origins of Life. ,vol. 14, pp. 383- 390 ,(1984) , 10.1007/BF00933681
Franco Cataldo, John Robert Brucato, Yeghis Keheyan, γ-Radiation Induced Polymerization of a Chiral Monomer: A New Way to Produce Chiral Amplification Origins of Life and Evolution of Biospheres. ,vol. 36, pp. 477- 485 ,(2007) , 10.1007/S11084-006-9031-8
F. Cataldo, Y. Keheyan, S. Baccaro, Gamma-radiolysis of chiral molecules: R(+)-limonene, S(-)-limonene and R(-)-a-phellandrene Journal of Radioanalytical and Nuclear Chemistry. ,vol. 262, pp. 423- 428 ,(2004) , 10.1023/B:JRNC.0000046772.22440.08