Boc-Tyr(TBu)-Aib-OH

Boc-Tyr(tBu)-Aib-OH is a dipeptide building block used in peptide synthesis, comprising L-tyrosine protected at the amino group with a tert-butyloxycarbonyl (Boc) group and at the hydroxyl with a tert-butyl (tBu) group, coupled to α-aminoisobutyric acid (Aib). Aib is a non-proteinogenic amino acid known to promote α-helix formation. The acid-labile Boc and tBu protecting groups allow selective deprotection during synthesis. This dipeptide introduces a preformed Tyr-Aib motif that can enhance peptide stability, secondary structure, or receptor binding. Its bulky tBu group on tyrosine adds steric effects that may influence peptide interactions. It is widely used in research on peptide conformation and in developing peptide therapeutics.

Appearance

• White to off-white solid or powder

Source

• Synthesized chemically, typically by coupling Boc-Tyr(tBu)-OH to Aib-OH or derivatives

Molecular Weight and Structure

• Molecular Weight: Approximately 448.55 g/mol

• Structure:

  • Boc (tert-butyloxycarbonyl) protects the N-terminal amino group

  • L-Tyrosine with tBu protection on hydroxyl group

  • α-Aminoisobutyric acid (Aib) with free C-terminal carboxyl group

Biological Activity

• Generally none inherent to the building block

• Activity depends on peptide incorporation

• Aib promotes α-helix formation, potentially affecting target interactions

• Tyrosine is common in bioactive peptides, allowing controlled introduction

Purity and Microbial Contamination

Identity and Quality Control

Shelf Life and Storage

Application

• Peptide synthesis for introducing Tyr-Aib motif

• α-helix induction via Aib incorporation

• Synthesis of peptidomimetics

• Research into peptide structure-function relationships

Key Characteristics

• Protected dipeptide of L-Tyrosine and Aib

• Acid-labile Boc and tBu protections

• Aib promotes α-helical structure formation

Citation

• https://pubmed.ncbi.nlm.nih.gov/12765333/

• https://pubmed.ncbi.nlm.nih.gov/17269831/

• https://pubmed.ncbi.nlm.nih.gov/17865333/

• https://pubmed.ncbi.nlm.nih.gov/15471369/

• https://pubmed.ncbi.nlm.nih.gov/19583199/

• https://pubmed.ncbi.nlm.nih.gov/20387915/

• https://pubmed.ncbi.nlm.nih.gov/15200271/

• https://pubmed.ncbi.nlm.nih.gov/19697497/

• https://pubmed.ncbi.nlm.nih.gov/16548674/

• https://pubmed.ncbi.nlm.nih.gov/20536178/