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Draw the structure of the protected amino acid that must

Chapter 25, Problem 25.81

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QUESTION:

Draw the structure of the protected amino acid that must be anchored to the solid support in order to use a Merrifield synthesis to prepare leucine enkephalin. (N terminus) Try-Gly-Gly-Phe-Leu (C terminus)

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QUESTION:

Draw the structure of the protected amino acid that must be anchored to the solid support in order to use a Merrifield synthesis to prepare leucine enkephalin. (N terminus) Try-Gly-Gly-Phe-Leu (C terminus)

ANSWER:

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This exercise tells us that a Merrifield synthesis is used to prepare leucine encephalin, which is a pentapeptide with the following structure: Try-Gly-Gly-Phe-Leu. Recall that by convention, when writing the structure of polypeptides the N-terminus is placed on the left and the C-terminus is placed on the right.

We're asked to draw the structure of the starting material for this Merrifield synthesis. In other words, we’re asked to draw the structure of the protected amino acid that must be anchored to the solid polymer resin support in order to begin the Merrifield synthesis of this pentapeptide.

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