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Friday_session_9 - for the reaction N O O O CO 2 Et O Cl 1...

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Chem 3580 – Spring 2009 Friday Session 9 1. Propose a reasonable synthesis for the sweetener Aspartame from the indicated starting compounds. H 2 N N H H O CO 2 H H Ph O OCH 3 N O O CO 2 Et CO 2 Et Br H 2 N OCH 3 O H Ph from and Aspartame 2. Using any of the peptide synthesis methods we have seen propose a reasonable synthesis for the amino acids (racemic) shown below. N H O O H 3 N O CH 3 HO O H H 3 N O NH 2 O (a) (b) (c) 3. Write down all the products of a single Edman degradation of the following: (a) Val-Ala-Cys (b) Ser-Asp (c) His-Thr-Pro-Lys (d) Tyr-Gly-Gly-Phe-Leu 4. The amino acid sequence of met-enkephalin, a brain peptide with powerful opiate- like biological activity, is Tyr-Gly-Gly-Phe-Met. What would be the product of step-by-step Edman degradation of met-enkephalin? 5. Provide the missing reagent (a) and formulate a detailed mechanism for the second step of the reaction. Cl (a) N O O O CO 2 Et CO 2 Et Na + N O O O CO 2 Et O 6. Write down the product of reaction shown below. H 2 N OH NH 2 O PhN=C=S (excess)
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Problems 7-9 are challenging. 7. The amino acid hydroxyproline can be synthesized as shown below. Propose a plausible mechanism
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Unformatted text preview: for the reaction. N O O O CO 2 Et O Cl 1. H 3 O + , ! 2. HO — , H 2 O N H HO O O Hydroxyproline 8. Suggest a mechanism for each of the steps involved in the reaction of D-glucose with aniline. O HO HO OH OH OH O HO HO OH NHPh OH O OH HO HO NHPh HO PhNH 2 H 2 O H + 9. When D-sorbose is treated with NH 3 D-amino glucose is obtained. Similarly, when the latter is treated with base ammonia is evolved with formation of D-sorbose. Suggest a mechanism. O OH OH HO OH HO NH 3 O HO HO NH 2 OH OH H 2 O + O HO HO NH 2 OH OH HO — , H 2 O O OH HO HO OH HO + NH 3 10. Conversion of 1,6-bisphosphate of D-sorbose (from D-glucose) into dihydroxyacetone diphosphate and glyceraldehyde 3-phosphate is one of the steps involved in the metabolism of carbohydrates. Propose a mechanism for this step. CH 2 OPO 3 O CH 2 OPO 3 O CH 2 OH + CHO OH CH 2 OPO 3 CH 2 OPO 3 HO OH OH...
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