CAS 117106-22-6

(2S)-2-Amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid

Description:

(2S)-2-Amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid, commonly referred to as Fmoc-L-lysine, is a protected amino acid used primarily in peptide synthesis. This compound features a lysine backbone, characterized by an amino group, a carboxylic acid group, and a side chain that contains an amino group. The Fmoc (9-fluorenylmethoxycarbonyl) group serves as a protective moiety, allowing for selective reactions during peptide assembly while preventing unwanted side reactions. The presence of the Fmoc group also facilitates the purification and characterization of peptides. This amino acid is typically white to off-white in appearance and is soluble in polar solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO). Its structure contributes to its role in forming stable peptide bonds, making it essential in the synthesis of various peptides and proteins in research and pharmaceutical applications. Overall, Fmoc-L-lysine is a valuable building block in the field of organic and medicinal chemistry.

Formula: C₁₉H₂₀N₂O₄

InChI: InChI=1S/C19H20N2O4/c20-17(18(22)23)9-10-21-19(24)25-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11,20H2,(H,21,24)(H,22,23)/t17-/m0/s1

InChI key: InChIKey=SWKHFSHBIZGRLP-KRWDZBQOSA-N

SMILES: C(OC(NCC[C@@H](C(O)=O)N)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2

Synonyms:

• (2S)-2-Amino-4-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)butanoic acid
• (2S)-2-Amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid
• Butanoic acid, 2-amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-
• Butanoic acid, 2-amino-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (S)-