Microsoft Word - Assignment-CHEM 4310P a g e | 1 Current Topics in Biochemistry/Bioorganic Chemistry Assignment This assignment is due Monday March XXXXXXXXXXby midnight on...

Assignment is attached as a file.


Microsoft Word - Assignment-CHEM 4310 P a g e | 1 Current Topics in Biochemistry/Bioorganic Chemistry Assignment This assignment is due Monday March 13 2023 by midnight on Blackboard as a single, legible PDF file. Your name and student number: 1. Describe a scientific experiment that shows evidence of how amino acids with slight enantiomeric excess could have eventually led to a amino acids with high enantioenrichment [3 marks]. P a g e | 2 2. Draw the following major product. In addition, draw the formation of three main by- products that arise due to quenching of the carbocation formed [6 marks]. P a g e | 3 3. In lecture you learned that biology uses an activation strategy to attach amino acids to tRNAs. Draw a plausible mechanism for the following reaction, and be sure to include the appropriate byproducts in the product mixture [6 marks]. . P a g e | 4 4. A series of dimeric peptides were synthesized to explore a strategy to target tumor cells (Bioconjugate Chem. 2011, 22, 1270-1278.). Draw the product of the following reaction sequence below. (Don’t forget stereochemistry.) [10 marks] 5. What conditions would you need to cleave the previous peptide (question 4) from the resin and remove all protecting groups [3 marks]. P a g e | 5 The Fmoc-protected rink amide resin is available commercially, and can be deprotonated in a 20% piperidine solution (Bioconjugate Chem. 2008, 19, 802-805.) to yield a primary amine. a. Draw a mechanism for the following transformation [ 5 marks]. P a g e | 6 b. From the deprotected rink-amide resin, design a c. Draw the product of the following a stereoselective synthesis for the peptide A below [13 marks].C-term thioester reaction [4 marks].