Organic Chemistry

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Phenylalanine

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Organic Chemistry

Definition

Phenylalanine is an essential amino acid that plays a crucial role in the structure and function of proteins. It is one of the 20 standard amino acids found in proteins and is also a precursor for the synthesis of other important compounds in the body.

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5 Must Know Facts For Your Next Test

  1. Phenylalanine is an aromatic amino acid, meaning it has a benzene ring in its side chain.
  2. It is considered an essential amino acid because the human body cannot synthesize it and must be obtained through the diet.
  3. Phenylalanine is a precursor for the synthesis of the neurotransmitter dopamine, as well as the pigment melanin.
  4. Deficiency of phenylalanine can lead to a condition called phenylketonuria, which can cause intellectual disability and other neurological problems if left untreated.
  5. The Edman Degradation technique utilizes phenylalanine's unique chemical properties to identify the amino acid sequence of a protein.

Review Questions

  • Explain the structural features of phenylalanine and how they contribute to its role in proteins.
    • Phenylalanine is an aromatic amino acid, meaning it has a benzene ring in its side chain. This unique structure allows phenylalanine to participate in various non-covalent interactions, such as pi-stacking and hydrophobic interactions, which are important for the stabilization of protein structures. The aromatic ring also makes phenylalanine a useful marker for identifying the amino acid sequence of proteins using techniques like the Edman Degradation.
  • Describe the importance of phenylalanine as an essential amino acid and its role in human health.
    • Phenylalanine is considered an essential amino acid because the human body cannot synthesize it and must be obtained through the diet. It is crucial for the synthesis of proteins, which are the building blocks of tissues and organs. Phenylalanine is also a precursor for the synthesis of important compounds like the neurotransmitter dopamine and the pigment melanin. Deficiency of phenylalanine can lead to a condition called phenylketonuria, which can cause intellectual disability and other neurological problems if left untreated. Maintaining adequate levels of phenylalanine through a balanced diet is essential for overall health and proper bodily function.
  • Explain the role of phenylalanine in the Edman Degradation technique for protein sequencing and how it contributes to our understanding of protein structure and function.
    • The Edman Degradation is a method used to determine the amino acid sequence of a protein by sequentially removing and identifying the amino acids from the N-terminus of the protein. Phenylalanine's unique chemical properties, particularly its aromatic side chain, make it a useful marker for this technique. The Edman Degradation relies on the specific reactivity of the N-terminal amino acid, which is then identified and removed, allowing the next amino acid in the sequence to be determined. By systematically identifying the amino acids in a protein, the Edman Degradation provides crucial information about the primary structure of the protein, which is essential for understanding its three-dimensional structure and ultimately its biological function within the body.
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