Tobacco smoke from a typical cigarette contains 20-40 ng of benzo[a]pyrene, which can be oxidized by mammalian metabolic enzymes to form cancerogenic and mutagenic compound A. Carcinogenic properties of compound A arise from its ability to react with 2-amino group of guanine base, an essential component of DNA, according to the following scheme. Propose the structure of compound A indicating the stereochemistry where appropriate. DNA NH DNA-NH2 НО, HO Compound A OH HO ОН HO ОН

Tobacco smoke from a typical cigarette contains 20-40 ng of benzo[a]pyrene, which can be oxidized by mammalian metabolic enzymes to form cancerogenic and mutagenic compound A. Carcinogenic properties of compound A arise from its ability to react with 2-amino group of guanine base, an essential component of DNA, according to the following scheme. Propose the structure of compound A indicating the stereochemistry where appropriate. DNA NH DNA-NH2 НО, HO Compound A OH HO ОН HO ОН

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...

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Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. CH3 GABA CO₂H CH3 dddd CH3 H₂N Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH3 CO₂H CH3 solddd CH3 CH3 2 CH₂ CO₂Et
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-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
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