Boc-L-Lys(ivDde)-OH is a protected lysine derivative in which the α-amino group is masked as a Boc carbamate and the ε-amino side chain is protected with an ivDde (ivDde = 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylidene) functionality. The molecule contains a free carboxylic acid group and a stereochemically defined lysine backbone consistent with the L configuration indicated in the name, while the side-chain ε-amino protection controls chemoselectivity by suppressing undesired amide or urea formation during peptide-coupling steps. In peptide synthesis workflows, this orthogonally protected lysine analogue is used as a building block that supports stepwise formation of lysine-containing sequences and provides a protected handle for selective deprotection and subsequent functionalization of the ε-amino group.
CAT No: CP26081
CAS No:862847-44-7
Synonyms/Alias:Boc-Lys(ivDde);N-alpha-Boc-N-epsilon-ivDde-L-lysine;Boc-l-lys(ivdde)-oh;862847-44-7;SCHEMBL21602782;MFCD07366801;AKOS030212172;F96447;(2S)-6-[[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-3-methylbutylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;N-alpha-t-Butyloxycarbonyl-N-epsilon-[1-(4,4-diMe-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine (Boc-L-Lys(ivDde)-OH)
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-epsilon-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine
Boc-L-Lys(ivDde)-OH is a protected lysine building block designed for peptide synthesis, featuring an N-terminal Boc group and a side-chain protected as an ivDde carbamate. The lysine side chain remains masked to prevent undesired reactions during chain assembly, while the ivDde group provides a commonly used orthogonal deprotection handle for selective functionalization at the lysine ε-position. This reagent is therefore used in workflows that require controlled installation of lysine side-chain substituents, including post-assembly derivatization and site-specific modification strategies.
1. Orthogonal Lysine Side-Chain Protection
Boc-L-Lys(ivDde)-OH supports peptide synthesis workflows where selective ε-functionalization of lysine is required after the main chain is assembled. Researchers using this reagent typically build peptide segments with the lysine side chain masked during coupling steps, then remove the ivDde protecting group at a chosen stage to enable installation of side-chain modifications without disturbing other protecting groups. This makes the reagent particularly relevant for generating peptides that contain lysine-dependent motifs such as conjugation-ready handles, attachment points for affinity tags, or controlled sites for downstream chemical biology studies.
2. Fmoc-Compatible Peptide Derivatization
Boc-L-Lys(ivDde)-OH is frequently selected for custom peptide manufacturing and research-grade peptide library construction when lysine ε-derivatization must be deferred until late-stage processing. By keeping the ε-amino functionality protected as an ivDde carbamate, the building block helps maintain chemoselectivity during standard peptide assembly and purification, while enabling a targeted lysine side-chain unlock step for subsequent conjugation chemistry. This approach is commonly used by peptide chemists developing modified peptide probes, receptor-binding peptide variants, or peptides requiring defined attachment chemistry for downstream labeling and immobilization.
3. Bioconjugate Linker Installation
Boc-L-Lys(ivDde)-OH is used to introduce a controlled lysine ε-amino site into peptides intended for bioconjugation workflows. After peptide assembly, removal of the ivDde group allows coupling of lysine side-chain derivatives such as amide-forming linkers, polymer attachment motifs, or other ε-NH functionalization reagents used to generate conjugates for chemical biology and biomaterials research. The protected lysine format helps reduce side reactions during synthesis and supports reproducible conjugation site placement, which is important for preparing defined peptide-biopolymer or peptide-surface constructs.
4. Peptide Intermediate For Lysine Functionalization
Boc-L-Lys(ivDde)-OH serves as a practical intermediate for preparing lysine-containing peptide building blocks that will undergo further side-chain elaboration. In medicinal chemistry and peptide drug discovery research, this enables the generation of analog series where the backbone sequence is fixed while the lysine ε-position is systematically varied through late-stage derivatization. The Boc-protected amino terminus and masked ε-amino group together support a controlled assembly-to-functionalization workflow, helping teams manage protecting-group compatibility across complex peptide designs and enabling efficient progression from synthesized peptide to final modified candidates.
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