Organic: lanosterol Biosynthetic Cyclization

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SUMMARY

The discussion focuses on the biosynthetic cyclization of oxidosqualene catalyzed by oxidosqualene cyclase (OSC), resulting in the formation of lanosterol. The reaction initiates with a protonation step, which is crucial for understanding the electron flow in the subsequent steps. Participants are encouraged to indicate the electron flow using curved arrows, starting from a bond or unshared electron pair and ending at an atom. Identifying the "hot spots" in the provided diagram is essential for accurately depicting the reaction mechanism.

PREREQUISITES
  • Understanding of organic chemistry reaction mechanisms
  • Familiarity with electron flow notation in chemical reactions
  • Knowledge of oxidosqualene and its role in biosynthesis
  • Experience with interpreting chemical diagrams and structures
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  • Research the detailed mechanism of oxidosqualene cyclase (OSC) action
  • Study the role of protonation in organic reactions
  • Learn about the significance of lanosterol in biological systems
  • Explore advanced topics in biosynthetic pathways of sterols
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Chemistry students, organic chemists, and biochemists interested in biosynthetic processes and reaction mechanisms involving sterol formation.

whatlifeforme
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This is a tough one!

Shown is the biosynthetic cyclization of oxidosqualene catalyzed by oxidosqualene cyclase (OSC) leading to lanosterol as the final product.

The reaction starts with a protononation step as shown. Indicate the flow of electrons after the initial protonation step leading to the product given.

Indicate the flow of electrons by starting your curved arrow at a bond or unshared electron pair.
In this question, the endpoint of your curved arrow will be an atom.
You should be able to find appropriate hot spots in the drawing.

[PLAIN]http://owl.cengage.com/mediaarchives/OrgChemJuly2009/Image/B7.28b.gif
 
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whatlifeforme said:
This is a tough one!

Shown is the biosynthetic cyclization of oxidosqualene catalyzed by oxidosqualene cyclase (OSC) leading to lanosterol as the final product.

The reaction starts with a protononation step as shown. Indicate the flow of electrons after the initial protonation step leading to the product given.

Indicate the flow of electrons by starting your curved arrow at a bond or unshared electron pair.
In this question, the endpoint of your curved arrow will be an atom.
You should be able to find appropriate hot spots in the drawing.

[PLAIN]http://owl.cengage.com/mediaarchives/OrgChemJuly2009/Image/B7.28b.gif[/QUOTE]

One way to start might be to count the hydrogens on each carbon?
 
Last edited by a moderator:

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