{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 33

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 33 - excess and...

Info icon This preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Chemical Biology 3OA3, September 2009 Page 33 E XPERIMENT 4 C ATALYSIS BY Y EAST : REDUCTION OF 1- PHENYL -1,2- PROPANEDIONE Introduction As noted in the introduction to Experiment 2, the use of biological methods to effect chemical transformations has proved useful in chemical synthesis, not least because of the spectacular control of selectivity that can be achieved. This is one example of integrating biology with chemistry, a field that has become known as chemical biology . In this experiment, you will use baker’s yeast ( Saccharomyces cerevisiae ) to reduce both carbonyl groups of 1-phenyl-1,2-propanedione ( 1 ), leading to 1-phenyl-1,2-propanediol ( 2 ) as the major product. In this process, two new stereogenic centres are produced from the achiral starting material. The major product is a single isomer, which is formed in > 98% enantiomeric
Image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: excess, and in high diastereomeric excess. It has the ( R ) configuration at C-1. You will establish the absolute configuration at C-2. O O OH O O OH OH OH 1 2 3 4 1 2 1 2 Start your report by drawing out the reaction scheme, showing all the possible stereoisomers of diol 2 , and labelling each chiral centre. Indicate which isomers have the R configuration at C-1. This reaction can proceed through two possible intermediates, ketols 3 and 4 . You need to bear this in mind when identifying your product How can the structure and stereochemistry of the product be confirmed? How is enantiomeric excess determined? These and other questions form an open-ended discussion that enables you to explore this aspect of chemical biology....
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern