Fmoc-Cit-OH

CAS: 133174-15-9

Ref. 3D-FF10665

Product Information

• Name: Fmoc-Cit-OH
• Synonyms: N-Fmoc-L-citrulline
• Brand: Biosynth
• Description: Fmoc-Cit-OH, or N-Fmoc-L-citrulline, is a protected amino acid derivative commonly used in peptide synthesis. The "Fmoc" portion refers to the fluorenylmethyloxycarbonyl group, a protecting group that shields the amino group of citrulline, preventing unwanted side reactions during peptide chain elongation. Citrulline, the core amino acid in Fmoc-Cit-OH, is a non-proteinogenic amino acid, which is not directly incorporated into proteins during translation. In peptide synthesis, Fmoc-Cit-OH is incorporated into peptide chains using solid-phase peptide synthesis (SPPS). This technique allows for the stepwise assembly of peptides on a solid support, with Fmoc-protected amino acids added sequentially. The Fmoc group is then removed using a mild base, exposing the free amino group for the addition of the next amino acid. Fmoc-Cit-OH is particularly valuable in the synthesis of peptides containing citrulline residues, which are often found in biologically active peptides and proteins. These peptides may have therapeutic potential in various fields, including drug discovery and prodrug synthesis.

Chemical properties

• Molecular weight: 397.42 g/mol
• Formula: C₂₁H₂₃N₃O₅
• Purity: Min. 98 Area-%
• Color/Form: White Off-White Powder
• InChI: InChI=1S/C21H23N3O5/c22-20(27)23-11-5-10-18(19(25)26)24-21(28)29-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,24,28)(H,25,26)(H3,22,23,27)/t18-/m0/s1
• InChI key: InChIKey=NBMSMZSRTIOFOK-SFHVURJKSA-N
• SMILES: NC(=O)NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O