(S)-6-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl)amino)hexanoic acid
97%
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description Product Description
This compound is a protected derivative of L-lysine used in solid-phase peptide synthesis (SPPS) for building complex peptides with stereochemical control. The ε-amino group (side chain) is protected with an Fmoc group, which is base-labile and can be selectively deprotected using mild bases like piperidine without affecting the peptide backbone. The α-amino group (N-terminal) is protected via an enamine linkage with a 4,4-dimethyl-2,6-dioxocyclohexylidene moiety and a 3-methylbutyl chain, removable under mild acidic conditions or with hydrazine, allowing orthogonal deprotection strategies.
The diketone functionality acts as a chromophore for UV monitoring of reactions and as a handle for potential further modifications. The bulky α-protecting group helps minimize aggregation, enhancing coupling efficiency and solubility in organic solvents. It is particularly valuable in pharmaceutical research for preparing biologically active peptides and peptidomimetics requiring precise side-chain manipulation.
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