Substance: Draw your substance here. From any source you like, choose a natural
ID: 828214 • Letter: S
Question
Substance: Draw your substance here.
From any source you like, choose a natural product (an organic compound or substance
produced by a living organism that is found in nature) with not more than 18 carbon atoms.
1. Draw the structure of your compound, report a name, the molecular formula and molar
mass. (5 pts.)
2. Cite one publication that describes the synthesis of this molecule. Use the information for
proper citations found under the following web address: (5 pts.)
http://library.williams.edu/citing/styles/acs.php
3. From this publication, select one synthetic step and describe it (narrative and drawing)
including the respective mechanism. Be sure to show pertinent information about this
particular reaction mechanism (arrows, reagents, conditions, stereochemistry). (10 pts.)
4. For the starting material used in the step you selected, identify the groups of homotopic
protons and from these, the group with the lowest and the group with the highest shift
values. Give an estimate for these shift values. Indicate any chiral centers. (10 pts.)
5. In not more than 50 words, describe the biochemical function of the natural product you
selected. (10 pts.)
Explanation / Answer
1. The name of the compound is palitaxel (taxol).
The molecular formula of the compound is
The molecular mass of the compound is 853.906 g/mol
2.The synthesis of the molecule is published as
Microtubules are cellular components that act as a skeleton for the cell. For cell division to occur, microtubules need to depolymerise back to tubulin. After that, tubulins repolymerise to form the spindle of cell division. The movement of the replicated chromosomes during mitosis depends on the spindle and therefore, the depolymerization of microtubules.
Paclitaxel or Taxol enhances the polymerization of tubulin to stable microtubules and also interacts directly with microtubules, stabilizing them against depolymerization. Hence, it interferes with the spindle formation process. Chromosomes are unable to move to the opposite sides of the dividing cells. Cells division is inhibited and eventually, cell death is induced.
C47H51NO14