Bis-Boc Lysine-Glutamate Conjugate: Properties & Applications
Bis-Boc Lysine-Glutamate Conjugate: Properties & Applications
1,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate is a bifunctionally protected, urea-linked amino acid conjugate that serves as a versatile building block for the synthesis of complex peptide architectures and peptidomimetic compounds in modern medicinal chemistry research.
- Chemical Name
- 1,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate
- SKU
- B1046896
- Core Linkage
- Urea (carbonyl-amino) linkage connecting the lysine-derived side chain to the L-glutamate nitrogen
- Protective Groups
- Multiple tert-butyl ester (Boc-type) groups protecting carboxylate and amine functionalities
- Stereochemistry
- L-configuration at the glutamate alpha-carbon; (1S)-configuration at the lysine-derived center
- Primary Application
- Protected building block for peptide synthesis, peptidomimetics, and medicinal chemistry
- Supplier
- Aladdin Scientific (SKU: B1046896)
Chemical Identity and Structural Features
1,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate is a structurally sophisticated, orthogonally protected amino acid conjugate. Its systematic name encodes several key structural elements: two tert-butyl (1,1-dimethylethyl) ester groups that protect the 1- and 5-carboxylate positions of the glutamate backbone, a urea-type carbonyl linkage bridging the glutamate nitrogen to a lysine-derived six-carbon chain, a free terminal primary amine at the epsilon position of the lysine-derived fragment, and a tert-butoxycarbonyl (Boc)-protected alpha-carboxylate on the lysine-derived moiety.
The compound belongs to the broader class of N-carbamoyl amino acid derivatives. The urea bond (–NH–C(=O)–NH–) is notable for its resistance to proteolytic degradation compared with a standard peptide amide bond, making such scaffolds attractive in peptidomimetic design. The L-stereochemistry at the glutamate alpha-carbon and the defined (1S)-configuration at the lysine-derived center confer chirality that is critical for biological recognition studies.
The multiple tert-butyl ester protecting groups can be removed simultaneously under mild acidic conditions (e.g., trifluoroacetic acid in dichloromethane), a feature that greatly simplifies deprotection workflows in multi-step synthetic sequences.
Role as a Building Block in Peptide and Medicinal Chemistry Synthesis
Protected amino acid conjugates of this type are indispensable tools in solid-phase and solution-phase peptide synthesis. The orthogonal protection strategy embodied in this compound—where multiple functional groups (amines, carboxylic acids) are masked by acid-labile tert-butyl and Boc groups—allows chemists to selectively introduce, couple, and deprotect functional handles in a controlled sequence.
The free terminal primary amine on the lysine-derived chain provides a reactive handle for further acylation, reductive amination, or coupling reactions, enabling the construction of branched or dendritic peptide architectures. Such branched structures are increasingly explored in the development of multivalent ligands, lipopeptide conjugates, and targeted drug-delivery scaffolds.
The urea linkage itself is of significant medicinal chemistry interest. Urea-containing peptidomimetics have been explored as inhibitors of various enzymes and protein-protein interaction targets, owing to the urea group's capacity to engage in multiple hydrogen-bond donor and acceptor interactions with binding-site residues. This compound therefore serves not only as a synthetic intermediate but also as a direct precursor to pharmacologically relevant scaffolds.
Handling, Storage, and Laboratory Safety Considerations
As with most multi-protected amino acid derivatives, 1,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate should be stored under appropriate conditions to preserve integrity of the acid-labile protecting groups. General best practices for such compounds include storage in a cool, dry environment, away from strong acids, bases, and moisture, preferably under inert gas (nitrogen or argon) if long-term storage is required.
Researchers should consult the product-specific Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use. Standard laboratory personal protective equipment (PPE)—including gloves, eye protection, and a laboratory coat—should be worn when handling the compound. Exposure to TFA or other strong acids used during deprotection steps requires additional precautions, including use of a chemical fume hood.
The compound should be allowed to equilibrate to room temperature before opening the container, to minimize moisture condensation on the solid material. Solutions should be freshly prepared where possible, particularly in protic solvents, to avoid ester hydrolysis or premature deprotection.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 1,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate under SKU B1046896. Researchers and procurement teams are encouraged to contact Aladdin Scientific directly for current specifications including purity grade, available pack sizes, certificate of analysis (CoA), and pricing information, as these parameters may be updated.
For synthetic applications requiring high stereochemical fidelity, it is advisable to verify the enantiomeric excess (ee) and chemical purity by established analytical methods such as HPLC with a chiral stationary phase, optical rotation measurement, and NMR spectroscopy prior to use in critical synthetic steps.
Aladdin Scientific's technical support team can assist with questions relating to compatibility, application protocols, and appropriate analytical characterization strategies for this compound and related amino acid building blocks.
Frequently asked questions
What is the significance of the urea linkage in this compound?
The urea (–NH–C(=O)–NH–) linkage connecting the lysine-derived chain to the glutamate nitrogen confers greater resistance to enzymatic (proteolytic) cleavage compared with a conventional peptide bond, making it a valuable structural motif in peptidomimetic and medicinal chemistry design. It also provides two hydrogen-bond donor NH groups and one acceptor carbonyl, enabling rich interactions with biological targets.
How are the tert-butyl ester protecting groups removed from this compound?
The tert-butyl ester groups in this compound are acid-labile and can typically be removed by treatment with trifluoroacetic acid (TFA) in dichloromethane (DCM), a standard and mild deprotection protocol widely used in Boc/tBu-based peptide synthesis strategies. Reaction conditions (TFA concentration, time, temperature) should be optimized based on the specific synthetic context to avoid side reactions.
What synthetic applications is this compound suited for?
This compound is suited for use as a protected building block in solution-phase and solid-phase peptide synthesis, construction of urea-containing peptidomimetics, preparation of branched or dendritic peptide scaffolds exploiting its free terminal amine, and as an intermediate in the synthesis of pharmacologically active compounds targeting enzyme active sites or protein-protein interactions.
How should this compound be stored to maintain stability?
The compound should be stored in a cool, dry location away from moisture, strong acids, and strong bases. For extended storage, an inert atmosphere (nitrogen or argon) is recommended to prevent degradation of the acid-sensitive protecting groups. Always consult the Aladdin Scientific Safety Data Sheet and Certificate of Analysis for product-specific storage recommendations.
References
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: New York, 2007.
- Albericio, F. Orthogonal protecting groups for N-alpha-amino and C-terminal carboxyl functions in solid-phase peptide synthesis. Biopolymers (Peptide Science) 2000, 55, 123–139.
- Lenci, E.; Trabocchi, A. Peptidomimetic toolbox for drug discovery. Chemical Society Reviews 2020, 49, 3262–3277.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）