Artificial Amino Acid

This week's assignment challenged us to synthesize our own amino acid. My amino acid is named 2-amino-3-phenyl-butanoic acid and is pictured below:

I would synthesize this amino acid by first reacting 2-phenylpropanol (Chem-Spider) with PCC in order to form an aldehyde which would then be reacted with ammonium chloride and sodium cyanide which would replace the aldehyde with an amino group and a cyano group. This intermediate would then be reacted with hydronium in order to form the final product, 2-amino-3-phenyl-butanoic acid (Williamson). The reaction scheme is pictured below:

We were also challenged to place our artificial amino acid (2-amino-3-phenyl-butanoic acid) within a pentapeptide with four amino acids which exist naturally. The pentapeptide begins with cysteine, continues with glycine, the synthetic amino acid is in the middle, histadine is the fourth amino acid, and the final amino acid is alanine. The pentapeptide is pictured below:

 

Sources:

Chem Spider. 2-phenylpropanol.  http://www.chemspider.com/Chemical-Structure.13657.html

Smith, J. G. Organic Chemistry, 3rd Ed.; McGraw-Hill: New-York, 2008.