In an effort to explore the activity of steroid-cyclizing enzymes, Compound X below was used as a substrate for oxidosqualene cyclase. Interestingly, the enzyme accepted this unnatural substrate and yielded Compound Y as the product. OMe oxidosqualene cyclase OMe Compound X I HO Compound Y a) Provide a complete curved-arrow mechanism for this transformation. While you do not have to show carbocation intermediates in the cyclization cascade, you must show the most stable resonance structure for any intermediate carbocations that result from this cascade prior to quenching. You do not have to account for the observed stereochemistry.
In an effort to explore the activity of steroid-cyclizing enzymes, Compound X below was used as a substrate for oxidosqualene cyclase. Interestingly, the enzyme accepted this unnatural substrate and yielded Compound Y as the product. OMe oxidosqualene cyclase OMe Compound X I HO Compound Y a) Provide a complete curved-arrow mechanism for this transformation. While you do not have to show carbocation intermediates in the cyclization cascade, you must show the most stable resonance structure for any intermediate carbocations that result from this cascade prior to quenching. You do not have to account for the observed stereochemistry.
Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter20: Enzymes
Section: Chapter Questions
Problem 20.11E: Match the following general enzyme names and reactions catalyzed: Enzyme Reaction catalyzed a....
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![In an effort to explore the activity of steroid-cyclizing enzymes, Compound X below was used
as a substrate for oxidosqualene cyclase. Interestingly, the enzyme accepted this unnatural substrate and
yielded Compound Y as the product.
OMe
oxidosqualene
cyclase
OMe
Compound X
I
HO
Compound Y
a) Provide a complete curved-arrow mechanism for this transformation. While you do not have to show
carbocation intermediates in the cyclization cascade, you must show the most stable resonance
structure for any intermediate carbocations that result from this cascade prior to quenching. You do not
have to account for the observed stereochemistry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F48fe4e77-f9ef-48e7-bc1d-608abf2bf6f8%2F9920571c-63ae-4967-a4de-7ccd2ea3fff7%2Fq18lq4o_processed.png&w=3840&q=75)
Transcribed Image Text:In an effort to explore the activity of steroid-cyclizing enzymes, Compound X below was used
as a substrate for oxidosqualene cyclase. Interestingly, the enzyme accepted this unnatural substrate and
yielded Compound Y as the product.
OMe
oxidosqualene
cyclase
OMe
Compound X
I
HO
Compound Y
a) Provide a complete curved-arrow mechanism for this transformation. While you do not have to show
carbocation intermediates in the cyclization cascade, you must show the most stable resonance
structure for any intermediate carbocations that result from this cascade prior to quenching. You do not
have to account for the observed stereochemistry.
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