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There are other, less dramatic examples of how differently the two enantiomers can affect our cells. Limonene, for example, is chiral, but the two enantiomers can be difficult to distinguish at first glance (figure 2). The receptors in our nose are more sensitive.
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nobelprize.org/nobel_prizes/chemistry/laureates/2001/pu...
nobelprize.org/nobel_prizes/chemistry/laureates/2001/public.html
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Enantiomers behave in the same way in ordinary test tube reactions. Physical properties like melting, density and solubility are also identical. But enantiomers behave differently when in the presence of other chiral molecules. ... Figure 17 - Limonene enantiomers ... enantiomers of limonene...
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scholar.hw.ac.uk/site/chemistry/topic7.asp?outline=
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J. 2002; 17: 59–63. DOI: 10.1002/ffj.1040. Antimicrobial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha ...
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doi.wiley.com/10.1002/ffj.1040
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Studies on the enantiomers of limonene, and later pinene, have shown that biological activity ..... enantiomers, yet it was when (+)-limonene was combined ...
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doi.wiley.com/10.1002/ffj.1843
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Limonene enantiomers and substrate analogs, including specifically fluorinated derivatives, were utilized to probe active site interactions with recombinant ...
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linkinghub.elsevier.com/retrieve/pii/S0003986100922483
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Our present results showing that there are sex-related differences in the oxidative metabolism of limonene enantiomers by liver microsomes may provide useful information on the basis of limonene-induced toxicities in different animal species.
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cat.inist.fr/?aModele=afficheN&cpsidt=13445492
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The regiochemistry and facial stereochemistry of the limonene-6-hydroxylase- (CYP71D18-) mediated hydroxylation of the monoterpene olefin limonene are determined by the absolute configuration of the substrate. ... Institute of Biological Chemistry, Washington State University, Pullman, ... Publication Date (Web): January 12, 2002...
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pubs.acs.org/doi/abs/10.1021/bi011717h
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(+)-Limonene is reported to cause nephropathy in male rats, but not in female rats and other species of animals including mice, rabbits, guinea pigs, and dogs. ... In this study, we investigated whether (+)- and (−)-limonene enantiomers are differentially metabolized by liver microsomes of male and female rats.
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pubs.acs.org/cgi-bin/abstract.cgi/crtoec/2002/15/i01/ab...
pubs.acs.org/cgi-bin/abstract.cgi/crtoec/2002/15/i01/abs/tx0155350.html
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The two enantiomers of carvone evoked overlapping but significantly distinct regions of glomerular activity; however, the activity patterns evoked by the enantiomers of limonene and of terpinen-4-ol were not statistically different from one another.
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www.jneurosci.org/cgi/content/full/21/24/9837
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