ОН YHO, ОН H. O, ОН NH2 This is the molecule commonly known as Doxorubicin. Doxorubicin is used in chemotherapy to inhibit uncontrolled cell growth, a hallmark of cancerous cells. Doxorubicin specifically inhibits an enzyme called topoisomerase which helps remove supercoils in DNA as DNA is replicated during cell growth and division (mitosis). Indicate the functional groups a part of Doxorubicin using the following key to label the different parts of the molecule (note not all functional groups listed may be a part of Doxorubicin): Carboxylic Acid label with a C Ketone label with a K Alcohol label with an A Ketal label with a T Aldehyde label with an H Ester label with an R Acetal label with an L Amine label with an M Amide label with a D Phenol label with a P Aromatic label with a B Ether label with an E
ОН YHO, ОН H. O, ОН NH2 This is the molecule commonly known as Doxorubicin. Doxorubicin is used in chemotherapy to inhibit uncontrolled cell growth, a hallmark of cancerous cells. Doxorubicin specifically inhibits an enzyme called topoisomerase which helps remove supercoils in DNA as DNA is replicated during cell growth and division (mitosis). Indicate the functional groups a part of Doxorubicin using the following key to label the different parts of the molecule (note not all functional groups listed may be a part of Doxorubicin): Carboxylic Acid label with a C Ketone label with a K Alcohol label with an A Ketal label with a T Aldehyde label with an H Ester label with an R Acetal label with an L Amine label with an M Amide label with a D Phenol label with a P Aromatic label with a B Ether label with an E
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter22: Organic And Biological Molecules
Section: Chapter Questions
Problem 10RQ
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Concept explainers
Carbohydrates
Carbohydrates are the organic compounds that are obtained in foods and living matters in the shape of sugars, cellulose, and starch. The general formula of carbohydrates is Cn(H2O)2. The ratio of H and O present in carbohydrates is identical to water.
Starch
Starch is a polysaccharide carbohydrate that belongs to the category of polysaccharide carbohydrates.
Mutarotation
The rotation of a particular structure of the chiral compound because of the epimerization is called mutarotation. It is the repercussion of the ring chain tautomerism. In terms of glucose, this can be defined as the modification in the equilibrium of the α- and β- glucose anomers upon its dissolution in the solvent water. This process is usually seen in the chemistry of carbohydrates.
L Sugar
A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotating the polarized light’s plane in the direction anticlockwise. L isomers are one of the 2 isomers formed by the configurational stereochemistry of the carbohydrates.
Question
Transcribed Image Text:**Doxorubicin Molecular Structure**
**Description:**
This image depicts the chemical structure of the molecule known as Doxorubicin. Doxorubicin is frequently utilized in chemotherapy to inhibit uncontrolled cell growth, a key characteristic of cancerous cells. It acts by specifically inhibiting an enzyme called topoisomerase, which assists in removing supercoils in DNA during replication, thus hindering cell growth and division (mitosis).
**Labeling Exercise:**
You are encouraged to identify and label the functional groups present in the Doxorubicin molecule using the following key. Please note that not all functional groups listed may be part of Doxorubicin:
- **A**: Alcohol
- **H**: Aldehyde
- **R**: Ester
- **P**: Phenol
- **C**: Carboxylic Acid
- **K**: Ketone
- **B**: Aromatic
- **T**: Ketal
- **L**: Acetal
- **M**: Amine
- **D**: Amide
- **E**: Ether
**Instructions:**
Examine the molecular structure and apply the appropriate labels to each functional group you identify within the Doxorubicin structure. This exercise facilitates a deeper understanding of organic chemistry and molecular biology as it applies to pharmacology and cancer treatment mechanisms.
Transcribed Image Text:**Image Transcription for Educational Website**
### Diagram Description:
The image displays a chemical structure of an abbreviated form of Doxorubicin. A prominent feature is the carbon ring with several functional groups attached. There are two oxygen atoms depicted within the ring, one of which is connected to an R group chain. An asterisk (*) marks a specific carbon atom which is part of this structure. Additionally, an amine group (NH2) and a hydroxyl group (OH) are attached to the structure. The diagram indicates that water (H2O) is a product of a reaction shown by an arrow.
### Educational Content:
- **Chemical Explanation:**
- The structure represents a partial view of Doxorubicin with a large portion of the molecule depicted as the 'R' carbon chain. The marked carbon atom is recognized as being part of a functional group already studied in chemistry courses.
- Students are tasked with creating a reaction scheme that begins with a single molecule containing an aldehyde and alcohol to form the shown intermediate. Additionally, the formation of the final product entails reaction with another alcohol molecule.
- **Biological Function:**
- Doxorubicin inhibits the enzyme topoisomerase and impedes DNA replication by disrupting intermolecular bonds within DNA strands through intercalation, where molecules insert themselves between DNA bases.
- The challenge includes identifying three potential types of intermolecular forces that Doxorubicin may establish with DNA, citing an example of a functional group from Doxorubicin capable of forming such a bond.
This detailed information provides a comprehensive understanding of Doxorubicin's structure, synthesis, and biological activity for educational purposes.
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