Define chemoenzymatic synthesis draw all 20 canonical

Question

Assignment -

1) Find a literature example of both:

a) a Glycosyl transferases

b) a glycosylases

That includes a mechanism. Draw and explain the step of the reaction.

2) Provide an example of a competitive reversible and an irreversible inhibitor of either class of carbohydrate enzyme.

Howe does the inhibitor work? Provide mechanistic details.

3) Provide the mechanism of a Swern oxidation.

4) Form β-glucose pentaacetate:

Provide a synthesis of this sugar-like molecule.

5) a) Define chemoenzymatic  synthesis.

b) Provide an example from the literature showing the starting material for the whole synthesis, the particular step using a chemoenzymatic approach, and then final product.

c) Why did they use a chemoenzymatic step?

6) Draw all 20 canonical amino acids, and label them. Be aware of Stereochemistry.

Draw 3 additional biologically common amino acids, and name them.

7) Provide protected amino acids (side chain) appropriate for a) Boc  and b) Fmoc solid -phase synthesis for all 20 AAs. (Note some of the side chains of courses don't  need protection). The link in the eniol should help. Note: you should draw out the full structure. Abbreviations are only helpful if you know what they mean.

8) Show deportation conditions + mechanism for the following common side chains:

• (For) (Used for Trp)
• (cyHx) (Used for Glu, Asp)
• (Xan) (Used for Asn) ← Note: why do we protect Asn but not Glu in Boc synthesis?

Use For lots

• (ODMAB) Use for Glu
• OPF_P Usefull for acids
• PbF (Arg)
• Dpm (Cys)

9) Here is tripeptide

Ser-Glu-His

Provide 6 different syntheses of this system.

10) Provide a mechanism for

a) CDI

b) DCC

c) HBTCl

couplings.

11) Provide am mechanism for:

12) How can you suppless racemization during synthesis Why is it a problem? (Why do we care?)

Need to see the steps of each solution.

Attachment:- Assignment File.rar