Specification
Description
Fmoc-Phe(Cl2)2-OH is a derivative of phenylalanine, which is an essential amino acid that must be consumed from external sources. Fmoc-Phe(Cl2)2-OH is a common building block in solid-phase peptide synthesis (SPPS) because it can be selectively deprotected and coupled to other amino acids. This compound was originally synthesized in 1997 by Barral et al. and has since become a widely used tool in peptide chemistry.
IUPAC Name
(2S)-3-[4-[bis(2-chloroethyl)amino]phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)N(CCCl)CCCl)C(=O)O
InChI
1S/C28H28Cl2N2O4/c29-13-15-32(16-14-30)20-11-9-19(10-12-20)17-26(27(33)34)31-28(35)36-18-25-23-7-3-1-5-21(23)22-6-2-4-8-24(22)25/h1-12,25-26H,13-18H2,(H,31,35)(H,33,34)/t26-/m0/s1
InChI Key
AVJVPROWJLZHME-SANMLTNESA-N
Application
Fmoc-Phe(Cl2)2-OH is commonly used in SPPS to synthesize peptides with biological activity. This compound is also used in medicinal chemistry to develop new drugs and small molecules. Fmoc-Phe(Cl2)2-OH has been used in a variety of scientific experiments, including studies of protein-protein interactions, drug discovery, and structure-activity relationship studies.
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine