1-(Triphenylmethyl)-L-histidine

• CAT Number: R062372
• CAS Number: 35146-32-8
• Molecular Formula: C25H23N3O2
• Molecular Weight: 397.478
• Purity: ≥95%
• Synonyms: (S)-2-Amino-3-(1-trityl-1H-imidazol-4-yl)propanoic Acid; 1-Trityl-L-histidine; ?N(im)-Trityl-L-histidine
• Storage: Store at -20°C
• IUPAC Name: (2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoic acid
• InChI: InChI=1S/C25H23N3O2/c26-23(24(29)30)16-22-17-28(18-27-22)25(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,17-18,23H,16,26H2,(H,29,30)/t23-/m0/s1
• InChIKey: BSZQZNOAYQCQFZ-QHCPKHFHSA-N
• SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=C(N=C4)CC(C(=O)O)N

1-(Triphenylmethyl)-L-histidine is a protected derivative of the amino acid L-histidine, where the nitrogen on the imidazole ring is blocked by a triphenylmethyl (trityl) group. This protective group is commonly used in peptide synthesis to prevent undesired side reactions involving the imidazole moiety during the assembly of peptides. After the synthesis is complete, the triphenylmethyl group can be selectively removed under mild conditions, revealing the functional histidine residue. This compound plays a critical role in creating complex peptides and proteins in research and pharmaceutical applications, particularly in solid-phase peptide synthesis (SPPS).