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Chapter 29: Q50P (page 1194)

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson鈥檚 disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Short Answer

Expert verified

The steps needed to convert A to L-dopa is shown as:

Step by step solution

01

L-dopa

L-dopa is an organic compound containing amino groups and is used to treat the symptoms linked with Parkinson鈥檚 disease.It can be synthesized from L-Tyrosine, and dopamine is synthesized from L-dopa.

02

Steps needed to convert A to L-dopa 

When A is treated with H2 in the presence of a chiral Rh catalyst, an alkene is reduced to alkane. On further treatment with a strong acid, the NHCOCH3(amide group) is converted toNH2 (amine group), the methoxy group to OH, and theCH3COO group to OH.

This leads to the formation of L-dopa. The steps required to convert A to L-dopa is shown as:

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Most popular questions from this chapter

After the peptide chain of collage has been formed, many of the proline residues are hydroxylated on one of the ring carbon atoms. Why is this process important for the triple helix of collagen?

Write out the steps for the synthesis of each peptide using the Merrifield method:

  1. Ala-Leu-Phe-Phe; (b) Phe-Gly-Ala-Ile.

What form exists at the isoelectric point of each of the following amino acids: (a) valine; (b)leucine; (c)proline; (d) glutamic acid.

Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

Draw all the steps in the synthesis of each peptide from individual amino acids:

  1. Gly-Ala;

  2. Ile-Ala-Phe
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