CAS 1185301-96-5

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-methoxy-α-methylphenylalanine

Description:

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-methoxy-α-methylphenylalanine, commonly referred to as Fmoc-3-methoxy-α-methylphenylalanine, is a derivative of the amino acid phenylalanine, modified for use in peptide synthesis. This compound features a fluorenylmethoxycarbonyl (Fmoc) protecting group, which is widely utilized in solid-phase peptide synthesis due to its stability under basic conditions and ease of removal under acidic conditions. The presence of the methoxy group at the 3-position of the phenyl ring enhances the compound's lipophilicity and can influence its interaction with biological targets. The α-methyl group contributes to steric hindrance, which can affect the conformation and reactivity of the peptide during synthesis. This compound is typically used in the preparation of peptides for research and pharmaceutical applications, particularly in studies involving protein structure and function. Its unique structural features make it a valuable building block in the field of medicinal chemistry and peptide design.

Formula: C₂₆H₂₅NO₅

InChI: InChI=1S/C26H25NO5/c1-26(24(28)29,15-17-8-7-9-18(14-17)31-2)27-25(30)32-16-23-21-12-5-3-10-19(21)20-11-4-6-13-22(20)23/h3-14,23H,15-16H2,1-2H3,(H,27,30)(H,28,29)

InChI key: InChIKey=BAQRRKLRSXHSAM-UHFFFAOYSA-N

SMILES: C(OC(NC(CC1=CC(OC)=CC=C1)(C(O)=O)C)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3

Synonyms:

• N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-methoxy-α-methylphenylalanine
• Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-methoxy-α-methyl-