Interpretation:
The mechanism of cationic intermediate formed by crosslinking of DNA (deoxyribonucleic acid) to mitomysin and the mechanism for the formation of dihydromitosene are to be represented.
Concept introduction:
舧 A nucleoside consists of a nucleobase (also termed as nitrogenous base), and a five-carbon sugar (either ribose or deoxyribose).
舧 A
舧 In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or N1 of a pyrimidine.
舧 Examples of nucleosides include cytidine, uridine, adenosine, guanosine and thymidine.
舧 Sugar (ribose/deoxyribose) and nitrogenous bases are linked through N-glycosidic bonds.
舧 These glycosidic bonds are formed by condensation reaction of first carbon of sugar molecule with the nitrogen atom
舧 This particular glycosidic bond is stable in basic solutions, but readily hydrolyzes in the presence of acids.
舧 DNA is the genetic material in human beings and most of the biological systems. The proportion of DNA is constant in all diploid human cells. However, gamete cells are haploid and are composed of half of the amount of DNA present in diploid cells.
舧 DNA exists in the form of a double stranded helix in which complementary bases are present opposite to each other and form base pairs.
舧 In most common form of DNA, that is, B-DNA,
舧 Mitomysin is an anticancer agent, which forms DNA crosslinks by binding to amino group of Guanine residue. It bears quinone moiety and aziridine ring along with the heterocyclic purine type ring. This quinone moiety undergoes reduction to form quinol, which cleaves its aziridine ring to form bond with guanine residue. Such bonding causes methylation of amino group in guanine. All these reactions are formed from a cationic intermediate, which is stabilized by quinol groups. Moreover, the intermediate can give rise to 1-dihydromitosene.
Want to see the full answer?
Check out a sample textbook solution
Chapter 25 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- How many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom moleculearrow_forwardIn the drawing area below, draw the major products of this organic reaction: 1. NaOH ? 2. CH3Br If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. No reaction. Click and drag to start drawing a structure. ☐ : A คarrow_forwardPredict the major products of the following organic reaction: NC Δ ? Some important Notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to draw bonds carefully to show important geometric relationships between substituents. Note: if your answer contains a complicated ring structure, you must use one of the molecular fragment stamps (available in the menu at right) to enter the ring structure. You can add any substituents using the pencil tool in the usual way. Click and drag to start drawing a structure. Х аarrow_forward
- Predict the major products of this organic reaction. Be sure you use dash and wedge bonds to show stereochemistry where it's important. + ☑ OH 1. TsCl, py .... 文 P 2. t-BuO K Click and drag to start drawing a structure.arrow_forwardConsider this organic reaction: ( Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. Click and drag to start drawing a structure. Х : а ค 1arrow_forwardIn the drawing area below, draw the major products of this organic reaction: If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. 1. NaH 2. CH3Br ? Click and drag to start drawing a structure. No reaction. : ☐ Narrow_forward
- + Predict the major product of the following reaction. : ☐ + ☑ ค OH H₂SO4 Click and drag to start drawing a structure.arrow_forwardConsider this organic reaction: ... OH CI Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. ☐ No Reaction. Click and drag to start drawing a structure. : аarrow_forwardConsider the following reactants: Br Would elimination take place at a significant rate between these reactants? Note for advanced students: by significant, we mean that the rate of elimination would be greater than the rate of competing substitution reactions. yes O no If you said elimination would take place, draw the major products in the upper drawing area. If you said elimination would take place, also draw the complete mechanism for one of the major products in the lower drawing area. If there is more than one major product, you may draw the mechanism that leads to any of them. Major Products:arrow_forward
- Draw one product of an elimination reaction between the molecules below. Note: There may be several correct answers. You only need to draw one of them. You do not need to draw any of the side products of the reaction. OH + ! : ☐ + Х Click and drag to start drawing a structure.arrow_forwardFind one pertinent analytical procedure for each of following questions relating to food safety analysis. Question 1: The presence of lead, mercury and cadmium in canned tuna Question 2: Correct use of food labellingarrow_forwardFormulate TWO key questions that are are specifically in relation to food safety. In addition to this, convert these questions into a requirement for chemical analysis.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning