Trt

Definition

Trt, or Temporary Removal Tag, is a key concept in the context of automated peptide synthesis using the Merrifield Solid-Phase Method. It refers to the temporary removal of protecting groups from specific amino acid residues during the stepwise assembly of a peptide chain on a solid support.

5 Must Know Facts For Your Next Test

1. The Trt (Temporary Removal Tag) is used to selectively deprotect the side-chain of specific amino acids during automated peptide synthesis, while keeping the N-terminal amino group protected.
2. The Trt group is typically used to protect the side-chain of cysteine, histidine, and tryptophan residues, which can undergo unwanted side reactions if left unprotected.
3. The Trt group is removed using mild acid conditions, such as trifluoroacetic acid (TFA), which selectively cleaves the Trt group without affecting the peptide-resin linkage or other protecting groups.
4. The selective deprotection of the Trt group allows for the subsequent coupling of the next amino acid to the deprotected side-chain, enabling the stepwise assembly of the desired peptide sequence.
5. The use of the Trt group is crucial in the Merrifield Solid-Phase Method, as it allows for the controlled and efficient synthesis of complex peptides with sensitive functional groups.

Review Questions

• Explain the purpose of the Trt (Temporary Removal Tag) in the context of automated peptide synthesis using the Merrifield Solid-Phase Method.
  • The Trt (Temporary Removal Tag) is used in automated peptide synthesis to selectively deprotect the side-chain of specific amino acids, such as cysteine, histidine, and tryptophan, while keeping the N-terminal amino group protected. This selective deprotection allows for the subsequent coupling of the next amino acid to the deprotected side-chain, enabling the stepwise assembly of the desired peptide sequence. The use of the Trt group is crucial in the Merrifield Solid-Phase Method, as it allows for the controlled and efficient synthesis of complex peptides with sensitive functional groups.
• Describe the process of removing the Trt group during the Merrifield Solid-Phase Method and explain its significance.
  • During the Merrifield Solid-Phase Method, the Trt group is removed using mild acid conditions, such as trifluoroacetic acid (TFA). This selective cleavage of the Trt group occurs without affecting the peptide-resin linkage or other protecting groups on the amino acid residues. The removal of the Trt group allows for the subsequent coupling of the next amino acid to the deprotected side-chain, facilitating the stepwise assembly of the desired peptide sequence. The ability to selectively deprotect specific amino acid residues is crucial in the Merrifield Solid-Phase Method, as it enables the synthesis of complex peptides with sensitive functional groups while maintaining the integrity of the growing peptide chain.
• Analyze the role of the Trt group in the context of the Merrifield Solid-Phase Method and explain how it contributes to the efficiency and versatility of automated peptide synthesis.
  • The Trt (Temporary Removal Tag) plays a pivotal role in the Merrifield Solid-Phase Method of automated peptide synthesis. By selectively deprotecting the side-chain of specific amino acids, such as cysteine, histidine, and tryptophan, the Trt group allows for the controlled and efficient assembly of complex peptide sequences. The selective deprotection of the Trt group, without affecting the peptide-resin linkage or other protecting groups, enables the stepwise coupling of amino acids, ultimately leading to the synthesis of the desired peptide. This level of control and versatility afforded by the Trt group is a key factor in the success of the Merrifield Solid-Phase Method, making it a widely used technique in the field of peptide synthesis.

Related terms

Solid-Phase Peptide Synthesis (SPPS): A method of peptide synthesis where the growing peptide chain is attached to an insoluble solid support, allowing for easy purification and automation of the synthesis process.

Protecting Groups:

Functional groups that are temporarily attached to reactive sites on amino acids to prevent unwanted side reactions during peptide synthesis.

Amino Acid Coupling: The process of forming a peptide bond between the carboxyl group of one amino acid and the amino group of another amino acid, resulting in the elongation of the peptide chain.