(S)-Benzyl 2,6-Diaminohexanoate Dihydrochloride: Key FAQs
(S)-Benzyl 2,6-Diaminohexanoate Dihydrochloride: Key FAQs
(S)-Benzyl 2,6-diaminohexanoate dihydrochloride is a protected L-lysine derivative in which the α-carboxyl group is benzyl-esterified and both amino groups are present as free amines, supplied as the dihydrochloride salt for enhanced stability and solubility in aqueous media.
- Chemical Name
- (S)-Benzyl 2,6-diaminohexanoate dihydrochloride
- SKU / Catalog Number
- B733086
- Compound Class
- L-Lysine benzyl ester dihydrochloride; protected amino acid derivative
- Stereochemistry
- (S)-configuration at the α-carbon, corresponding to the natural L-lysine stereocenter
- Salt Form
- Dihydrochloride salt, improving hygroscopic stability and aqueous solubility
- Primary Application
- Chiral building block in peptide synthesis, medicinal chemistry, and material science
What Is (S)-Benzyl 2,6-Diaminohexanoate Dihydrochloride?
(S)-Benzyl 2,6-diaminohexanoate dihydrochloride is the benzyl ester of L-lysine supplied as a dihydrochloride salt. In this compound, the carboxylic acid group of L-lysine is protected as a benzyl ester, leaving both the α-amino and ε-amino groups available for selective chemical manipulation. The (S)-configuration at the α-carbon is consistent with the naturally occurring L-lysine stereochemistry. The dihydrochloride salt form protonates both amine groups, significantly improving the compound's hygroscopic stability and its solubility in polar solvents such as water, methanol, and dimethylformamide (DMF).
This structural profile makes the compound a versatile chiral synthon widely employed in the preparation of lysine-containing peptides, peptidomimetics, and other nitrogen-rich scaffolds used in drug discovery and chemical biology research.
Research Applications and Use Cases
(S)-Benzyl 2,6-diaminohexanoate dihydrochloride serves several important roles in synthetic chemistry and life science research:
- Peptide synthesis: The compound acts as an α-carboxyl-protected lysine building block. The benzyl ester can be removed cleanly by catalytic hydrogenolysis (e.g., Pd/C, H₂), making it compatible with standard Boc/Cbz solid-phase or solution-phase peptide synthesis strategies.
- Medicinal chemistry: It is used as a chiral starting material for the synthesis of lysine analogs, prodrugs, and lysine-mimetic pharmacophores targeting enzymes such as histone deacetylases (HDACs) and aminopeptidases.
- Materials science and polymer chemistry: Diamine-containing lysine esters serve as monomers or crosslinkers in the preparation of biodegradable polyamides and polypeptide-based materials.
- Chemical biology: The two orthogonally addressable amine groups allow selective labeling, acylation, or conjugation reactions for the preparation of probes, conjugates, and modified substrates.
Handling, Storage, and Stability
As a dihydrochloride salt of a diamine-containing amino acid ester, (S)-Benzyl 2,6-diaminohexanoate dihydrochloride should be handled and stored with the following precautions:
- Storage temperature: Store at 2–8 °C (refrigerator) in a tightly sealed container under an inert atmosphere or with a desiccant to minimize moisture uptake. Confirm exact storage conditions from the product Certificate of Analysis (CoA).
- Hygroscopicity: The salt form reduces but does not eliminate hygroscopicity. Weigh and handle the material in a low-humidity environment or glovebox when high accuracy is required.
- Solubility: The dihydrochloride salt is freely soluble in water and polar protic solvents (methanol, ethanol). Solubility in DMF and DMSO has been reported for related lysine ester dihydrochloride salts; verify empirically for your specific application.
- Stability: Benzyl esters are susceptible to hydrolysis under strongly acidic or strongly basic conditions; prepare solutions freshly and avoid prolonged exposure to extremes of pH.
- Personal protective equipment: Standard laboratory PPE (gloves, safety glasses, lab coat) is recommended. Consult the Safety Data Sheet (SDS) for full hazard information.
Ordering and Purity Information
(S)-Benzyl 2,6-diaminohexanoate dihydrochloride is available from Aladdin Scientific under catalog number B733086. When placing an order or evaluating the reagent, researchers should consider the following:
- Purity: Confirm the purity grade from the product CoA available on the Aladdin Scientific website. For sensitive synthetic applications, HPLC-grade purity (≥98%) is generally recommended; verify the specific purity listed for lot B733086.
- Available pack sizes: Contact Aladdin Scientific customer service or check the product page for current pack-size options and pricing.
- Quality documentation: A Certificate of Analysis (CoA) including NMR, HPLC, and optical rotation data is typically available upon request. Optical rotation should confirm the (S)-configuration.
- Lead time: Standard items are typically dispatched within the lead time stated on the product page. Contact customer service for bulk or custom quantity inquiries.
Frequently asked questions
What is the molecular structure and stereochemistry of (S)-Benzyl 2,6-diaminohexanoate dihydrochloride?
(S)-Benzyl 2,6-diaminohexanoate dihydrochloride is the benzyl ester of L-lysine, where the carboxylic acid of lysine is protected as a benzyl ester and both the α-amine and ε-amine are present in their free-base forms, protonated as the dihydrochloride salt. The (S)-configuration at the α-carbon corresponds to the naturally occurring L-lysine stereocenter, making this compound an enantiopure chiral building block suitable for asymmetric synthesis.
How do I remove the benzyl ester protecting group after synthesis?
The benzyl ester group in (S)-Benzyl 2,6-diaminohexanoate dihydrochloride can be removed by catalytic hydrogenolysis using palladium on carbon (Pd/C) under hydrogen gas (H₂) atmosphere in a protic solvent such as methanol or ethanol. This method is mild and selective, leaving other sensitive functional groups intact under standard conditions. Alternatively, transfer hydrogenation using ammonium formate as the hydrogen donor with Pd/C has been reported for related benzyl esters; confirm compatibility with your specific substrate and conditions.
What solvents are recommended for dissolving (S)-Benzyl 2,6-diaminohexanoate dihydrochloride?
As a dihydrochloride salt, this compound shows good solubility in water and polar protic solvents including methanol and ethanol. It is also expected to dissolve in highly polar aprotic solvents such as DMF and DMSO, consistent with behavior reported for structurally analogous lysine ester dihydrochloride salts. Solubility in non-polar solvents such as diethyl ether or hexane is expected to be negligible. Always verify solubility empirically under your specific experimental conditions.
Is (S)-Benzyl 2,6-diaminohexanoate dihydrochloride the same as L-lysine benzyl ester dihydrochloride?
Yes. (S)-Benzyl 2,6-diaminohexanoate dihydrochloride is the IUPAC-based systematic name for L-lysine benzyl ester dihydrochloride. Both names describe the same compound: the benzyl ester of the (S)-enantiomer of 2,6-diaminohexanoic acid (lysine), supplied as the dihydrochloride salt. Researchers may encounter either name in the literature or supplier catalogs.
What quality documentation is available for catalog number B733086?
Aladdin Scientific typically provides a Certificate of Analysis (CoA) for each lot of B733086, which may include data such as HPLC purity, NMR spectral confirmation, and optical rotation to verify the (S)-stereochemistry. An Safety Data Sheet (SDS) is also available. Please contact Aladdin Scientific customer service or visit the product page to request lot-specific documentation.
References
- General reference: Greenstein, J.P.; Winitz, M. Chemistry of the Amino Acids. Wiley, New York, 1961. (Background on lysine chemistry and derivatives.)
- Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis, 2nd ed. Springer-Verlag, Berlin, 1994. (Benzyl ester protecting groups in peptide synthesis.)
- Aladdin Scientific product page for B733086: (S)-Benzyl 2,6-diaminohexanoate dihydrochloride. https://www.aladdinsci.com (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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