Boc-His(Boc)-Aib-OH

Boc-His(Boc)-Aib-OH is a protected dipeptide building block used in peptide synthesis to introduce histidine and α-aminoisobutyric acid (Aib) residues. Histidine’s α-amino group and imidazole side chain are protected with tert-butyloxycarbonyl (Boc) groups, allowing for strong acid-labile deprotection during synthesis. Aib is known for promoting α-helical conformations, improving peptide stability. This building block is valuable in creating peptides with metal-binding histidine residues and helical structure features.

Appearance

• White to off-white solid powder.

Source

• Synthetic chemical production.

• Commercially available from peptide reagent suppliers.

Molecular Weight and Structure

• Molecular weight approximately 455.5 g/mol (C20H32N4O6).

• Composed of Boc-protected histidine linked to Aib, with a free carboxyl terminus.

Biological Activity

• Biologically inactive by itself; activity depends on peptide incorporation.

• After deprotection, histidine side chain can bind metals or catalyze reactions.

• Aib induces helical peptide structure.

Purity and Microbial Contamination

• Purity ≥ 95% by HPLC.

• Minimal microbial contamination; tested by LAL endotoxin and sterility assays.

Identity and Quality Control

• Confirmed by mass spectrometry (MS), ¹H and ¹³C NMR.

• IR spectroscopy confirms key functional groups.

• Optical rotation confirms chiral purity.

• Amino acid analysis confirms sequence accuracy.

• Purity checked by HPLC.

Shelf Life and Storage

Application

• Solid-phase peptide synthesis to introduce His and Aib.

• Synthesis of metal-binding peptides or catalytically active sequences.

• Creation of α-helical peptide motifs.

• Peptidomimetic design.

Key Characteristics

• Boc protection ensures acid-labile removal; side chain His protection uncommon and allows stronger deprotection.

• Aib promotes helicity and stability.

• Soluble in organic solvents like DMF, DMSO, and acetonitrile.

• Enables synthesis of peptides with tailored biological and structural properties.

Citation

• Search “Boc-His(Boc)” + “peptide synthesis” for direct use cases.

• “Boc peptide synthesis” + “acid-labile protection.”

• “Aib peptide helix” and “α-aminoisobutyric acid conformation.”

• “Metal-binding peptides histidine.”

• Supplier technical data and peptide synthesis manuals.

• Chemical databases such as Reaxys, SciFinder.

• Google Scholar keywords: “Boc-His(Boc)-Aib-OH synthesis,” “Boc peptide synthesis,” “metal-binding peptide histidine,” “Aib peptide stability.”