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.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.25P
icon
Related questions
Question
None
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.
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.
Expert Solution
steps

Step by step

Solved in 2 steps

Blurred answer
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning