Chemical Forums

Specialty Chemistry Forums => Biochemistry and Chemical Biology Forum => Topic started by: fragmented3 on February 06, 2020, 10:21:29 PM

Title: Claisen Condensation and polyketide synthesis
Post by: fragmented3 on February 06, 2020, 10:21:29 PM

In class, we learned about claisen condensation of dicarbonyl compounds. My professor asked a question about claisen condensation applied to polyketide synthases, specifically, that of Erythronolide B. I have no clue how to answer this question, but I have gotten somewhere with my research..

The question was: How does the Claisen Condensation reaction proceed without a strong base in a cell, and why does nature select thioesters instead of esters for the transformation

My answer is: Thioesters are more reactive than esters because of the double bond between sulfur and carbon. Since sulfur is a row 3 compound, the sizing between the carbon and sulfur is very different than that of carbon and oxygen, therefore, it is not as stabilized as a double bonded oxygen to carbon, making the alpha proton more acidic.

As for why the claisen condensation proceeds without a strong base in a cell, I'm not sure how to answer that

Any help would be appreciated, thank you!

Title: Re: Claisen Condensation and polyketide synthesis
Post by: billnotgatez on February 07, 2020, 12:13:28 AM

We only post a given question once on the forum.
This is a forum policy.
Click on the link near the top center of the forum page.
Forum Rules: Read This Before Posting.
http://www.chemicalforums.com/index.php?topic=65859.0 (http://www.chemicalforums.com/index.php?topic=65859.0)

topic locked here see organic