Dde-D-Lys(Fmoc)-OH is a protected, amino acid derivative based on D-lysine featuring an Nα-(Fmoc) protecting group and an additional Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl) protecting group on the remaining amino functionality. The molecule contains both an amino group and a carboxyl group, with the lysine side chain retaining its aliphatic carbon chain that bears the protected amine, while the Fmoc and Dde groups control chemoselectivity by suppressing unprotected nucleophilicity during stepwise assembly. In peptide synthesis workflows, this protected lysine analogue is used as a building block for introducing a lysine residue with orthogonal deprotection handles, supporting selective side-chain functionalization and preparation of more complex peptide derivatives.
CAT No: CP25293
CAS No:1301706-71-7
Synonyms/Alias:1301706-71-7;N-alpha-Dde-N-epsilon-Fmoc-D-lysine;Dde-D-Lys(Fmoc);D-Lysine, N2-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-N6-[(9H-fluoren-9-ylmethoxy)carbonyl];(2R)-2-{[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino}-6-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid;(2R)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)ethylideneamino]hexanoic acid;MFCD11616545;BCC70671;N6-(((9H-fluoren-9-yl)methoxy)carbonyl)-N2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)-D-lysine;AKOS030212368;AS-80157;CS-0356289;F90128
Chemical Name:N-alpha-(4-4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-epsilon-(9-fluorenylmethyloxycarbonyl)-D-lysine
Dde-D-Lys(Fmoc)-OH is a chiral lysine derivative bearing an Fmoc-protected alpha-amino group and a Dde-protected side-chain amine, with a free carboxylic acid suitable for peptide coupling chemistry. The molecule combines two orthogonal nitrogen protecting groups: Fmoc for base-labile N-terminal deprotection during solid-phase peptide synthesis, and Dde for selective side-chain amine unmasking under mild hydrazine-type conditions, enabling controlled formation of lysine side-chain functionalities. The lysine backbone introduces a stereogenic center at the alpha carbon (D-configuration), while the side-chain protected amine provides a latent nucleophile that can be revealed for subsequent derivatization or for maintaining orthogonality in multi-step syntheses. The presence of an Fmoc aromatic carbamate and an acid handle for acylation makes this compound a practical chiral building block and protected amino acid intermediate for downstream peptide analog construction and functional group installation.
1. Peptide Synthesis
Dde-D-Lys(Fmoc)-OH is used in peptide building block preparation for both solution-phase and solid-phase peptide synthesis where orthogonal lysine protection is required. The Fmoc group supports standard N-terminal coupling cycles, while the Dde-protected side-chain amine remains masked to prevent undesired side reactions during chain assembly. The free carboxylic acid participates in peptide bond formation using common coupling strategies, and the D-lysine stereochemistry enables incorporation of D-amino acid residues into peptide sequences to modulate backbone conformation and proteolytic stability. Lysine side-chain unmasking after chain assembly can then enable targeted side-chain functionalization or controlled formation of lysine-dependent motifs in peptide science.
2. Side-Chain Functionalization
Dde-D-Lys(Fmoc)-OH is suitable for amino acid modification workflows that require selective activation of the lysine side-chain amine after Fmoc removal. The Dde protecting group provides a chemoselective handle for revealing the epsilon-amino functionality without disturbing the peptide N-terminus protection state, supporting stepwise installation of acyl, sulfonyl, carbamoyl, or linker groups. The latent side-chain nucleophile can be used to generate conjugation-ready intermediates for constructing amide-linked derivatives, charged pharmacophore mimics, or attachment points for molecular scaffolds. Orthogonality between Fmoc and Dde strategies helps maintain structural integrity during sequential derivatization, which is central to amino acid chemistry and peptidomimetic construction.
3. Bioconjugation Chemistry
Dde-D-Lys(Fmoc)-OH can serve as a protected amino acid precursor in chemical biology programs that build lysine-containing conjugates with defined attachment geometry. The lysine side-chain amine, once unmasked from the Dde group, can be converted into reactive intermediates for coupling to electrophiles such as activated esters, isothiocyanates, aldehyde-derived linkers, or other electrophilic conjugation partners. The D-configuration and the ability to control which nitrogen is exposed during synthesis can influence conjugate charge distribution and stability in biomolecular labeling contexts. Downstream formation of well-defined lysine-based linkages supports reproducible preparation of peptide conjugates, affinity probes, and labeled molecular tools used in biochemical research.
4. Peptidomimetics And SAR
Dde-D-Lys(Fmoc)-OH is applied in peptidomimetic and structure-activity relationship studies where D-lysine incorporation and orthogonally protected side chains enable systematic scaffold diversification. The combination of Fmoc and Dde protection supports iterative synthesis of analog series with controlled lysine modification patterns, including side-chain acylation, linker installation, and charge-tuning substitutions. The stereochemical integrity of the D-alpha carbon is maintained through peptide coupling, allowing SAR campaigns to attribute changes in properties to defined stereochemical and functional group variations. The resulting analogs can be used as research-grade intermediates for evaluating structure-function relationships in amino acid and peptide science.
5. Pharmaceutical Manufacturing Intermediates
Dde-D-Lys(Fmoc)-OH is relevant to pharmaceutical manufacturing and fine chemical production where protected amino acid intermediates are required for controlled, scalable peptide intermediate synthesis. The acid functionality supports reproducible conversion into activated species for peptide coupling, while the orthogonal Fmoc/Dde protection scheme supports manufacturing workflows that separate N-terminal deprotection from side-chain unmasking. The lysine side-chain amine protection strategy helps manage impurity formation by preventing premature crosslinking or overreaction during multi-step processing. Downstream, the protected lysine building block can be used to generate defined peptide fragments and peptidic intermediates that feed into larger synthetic sequences for industrial chemical manufacturing.
1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
2. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
3. High fat diet and GLP-1 drugs induce pancreatic injury in mice
4. Implications of ligand-receptor binding kinetics on GLP-1R signalling
5. The spatiotemporal control of signalling and trafficking of the GLP-1R
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More