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N² H 0 HA H₂N_ CH HN H N R H 0=0 -N: N R N R NH 12H1 N²H #2 OH AN. N zd R но HN H₂N. 0 2 EN R 3. A seminal paper on the reaction of singlet oxygen with the DNA base guanine was published by C.S. Foote et al. in 2004, less than two years before his untimely death (J. Am. Chem. Soc. 2004, 126, 16777–16782). Please read this paper and answer the following questions. As an aside, if you like a difficult NMR puzzle, you might enjoy this paper which is a masterpiece of structure determination by NMR. (a) Provide a mechanism for the formation of 8-oxo-G from guanine and singlet oxygen; your class notes may be helpful. (b) The authors found that the 8-oxo-G adduct from singlet oxygen and guanine reacts further to an unusual spiro compound. Starting with the 8-oxo-G molecule, show by means of a reaction equation the product and the key intermediate (characterized by low temperature NMR) of this process. Note that this just requires careful reading of the paper. You do not need to redraw the entire multi-step mechanism, just the starting compound, the intermediate, and the product.

N² H 0 HA H₂N_ CH HN H N R H 0=0 -N: N R N R NH 12H1 N²H #2 OH AN. N zd R но HN H₂N. 0 2 EN R 3. A seminal paper on the reaction of singlet oxygen with the DNA base guanine was published by C.S. Foote et al. in 2004, less than two years before his untimely death (J. Am. Chem. Soc. 2004, 126, 16777–16782). Please read this paper and answer the following questions. As an aside, if you like a difficult NMR puzzle, you might enjoy this paper which is a masterpiece of structure determination by NMR. (a) Provide a mechanism for the formation of 8-oxo-G from guanine and singlet oxygen; your class notes may be helpful. (b) The authors found that the 8-oxo-G adduct from singlet oxygen and guanine reacts further to an unusual spiro compound. Starting with the 8-oxo-G molecule, show by means of a reaction equation the product and the key intermediate (characterized by low temperature NMR) of this process. Note that this just requires careful reading of the paper. You do not need to redraw the entire multi-step mechanism, just the starting compound, the intermediate, and the product.

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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N² H 0 HA H₂N_ CH HN H N R H 0=0 -N: N R N R NH 12H1 N²H #2 OH AN. N zd R но HN H₂N. 0 2 EN R
Transcribed Image Text:N² H 0 HA H₂N_ CH HN H N R H 0=0 -N: N R N R NH 12H1 N²H #2 OH AN. N zd R но HN H₂N. 0 2 EN R
3. A seminal paper on the reaction of singlet oxygen with the DNA base guanine was published by C.S. Foote et al. in 2004, less than two years before his untimely death (J. Am. Chem. Soc. 2004, 126, 16777–16782). Please read this paper and answer the following questions. As an aside, if you like a difficult NMR puzzle, you might enjoy this paper which is a masterpiece of structure determination by NMR. (a) Provide a mechanism for the formation of 8-oxo-G from guanine and singlet oxygen; your class notes may be helpful. (b) The authors found that the 8-oxo-G adduct from singlet oxygen and guanine reacts further to an unusual spiro compound. Starting with the 8-oxo-G molecule, show by means of a reaction equation the product and the key intermediate (characterized by low temperature NMR) of this process. Note that this just requires careful reading of the paper. You do not need to redraw the entire multi-step mechanism, just the starting compound, the intermediate, and the product.
Transcribed Image Text:3. A seminal paper on the reaction of singlet oxygen with the DNA base guanine was published by C.S. Foote et al. in 2004, less than two years before his untimely death (J. Am. Chem. Soc. 2004, 126, 16777–16782). Please read this paper and answer the following questions. As an aside, if you like a difficult NMR puzzle, you might enjoy this paper which is a masterpiece of structure determination by NMR. (a) Provide a mechanism for the formation of 8-oxo-G from guanine and singlet oxygen; your class notes may be helpful. (b) The authors found that the 8-oxo-G adduct from singlet oxygen and guanine reacts further to an unusual spiro compound. Starting with the 8-oxo-G molecule, show by means of a reaction equation the product and the key intermediate (characterized by low temperature NMR) of this process. Note that this just requires careful reading of the paper. You do not need to redraw the entire multi-step mechanism, just the starting compound, the intermediate, and the product.
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