Artificial Amino Acid (Tigerine)

Common Name: Tigerine

IUPAC name: 2-amino-3,5-dimethylhexanoic acid

Figure 1. Tigerine

*Pictures made on ACD Chemsketch

Facts:

· This amino acid is found only on Campbellsville University’s campus!

Basic amino acids play a role in muscle cells and other tissues along with chemical processes such as neurotransmitter transport (1). Tigerine stimulate the muscles of CU students and spreads TIGER PRIDE throughout their bodies. This help students to succeed at CU.

This amino acid is essential for CU students!

Synthesis of Tigerine:

Synthesis of this particular amino acid is done through Strecker amino acid synthesis. Adolph Strecker founded this process, which synthesizes an amino acid from a aldehyde or ketone (2). The mechanism for Tigerine can be seen below in figure 2.

Figure 2. Mechanism for the Synthesis of Tigerine

Pentapeptide structure:

To make a peptide bond, the –OH portion of the carboxylic acid and one of the –H from the amine will break off and form water. This allows the nitrogen from the amine and the carbon from the carboxylic acid to connect (3). Figure 3 shows Tigerine connecting with 4 other amino acids in a C-G-(Tigerine)-H-A pentapeptide chain structure.

Figure 3. Pentapeptide Chain with Tigerine