(S)-α-Amino-γ-butyrolactone HCl: Properties & Lab Use
(S)-α-Amino-γ-butyrolactone HCl: Properties & Lab Use
(S)-α-Amino-γ-butyrolactone hydrochloride is a chiral, enantiomerically defined amino lactone hydrochloride salt widely used as a versatile building block in asymmetric synthesis, peptide chemistry, and the preparation of homoserine-derived natural product analogues.
- Chemical Name
- (S)-α-Amino-γ-butyrolactone hydrochloride
- SKU
- A101211
- Compound Class
- Chiral amino lactone hydrochloride salt; amino acid derivative
- Stereochemistry
- S-configuration at the α-carbon (single enantiomer)
- Primary Applications
- Asymmetric synthesis, peptide building block, homoserine lactone analogue preparation
- Physical Form
- Solid (hydrochloride salt)
What Is (S)-α-Amino-γ-butyrolactone Hydrochloride?
(S)-α-Amino-γ-butyrolactone hydrochloride is the hydrochloride salt of the cyclic lactone derived from L-homoserine. The molecule contains a five-membered γ-butyrolactone ring with an amino group at the α-position and a defined S-stereocenter, making it a single-enantiomer chiral building block. As a hydrochloride salt, it offers improved stability and handling characteristics compared with the free base form. Its structural resemblance to natural amino acids and its reactive lactone carbonyl make it a versatile intermediate in organic and medicinal chemistry.
Key Applications in Research and Synthesis
(S)-α-Amino-γ-butyrolactone hydrochloride serves several important roles in laboratory research:
- Asymmetric synthesis: The defined S-stereocenter allows chemists to introduce chirality into target molecules with high stereocontrol, making this compound a valuable chiral synthon.
- Peptide chemistry: The compound can function as a non-proteinogenic amino acid building block or as a masked homoserine equivalent, enabling the preparation of constrained peptide analogues.
- Natural product synthesis: Its structural relationship to homoserine lactones makes it relevant to the synthesis of quorum-sensing signal molecules and related natural products.
- Medicinal chemistry: The reactive lactone ring can be opened selectively by nucleophiles (amines, thiols, alcohols), providing rapid access to diversely functionalized amino acid scaffolds.
Handling, Storage, and Stability
As a hygroscopic solid hydrochloride salt containing a reactive lactone functionality, (S)-α-Amino-γ-butyrolactone hydrochloride requires careful handling:
- Storage: Store in a tightly sealed container under cool, dry conditions, protected from moisture and light. Refrigerated storage (2–8 °C) is generally recommended to maximize shelf life; consult the product Certificate of Analysis for lot-specific recommendations.
- Moisture sensitivity: Lactones are susceptible to hydrolysis under aqueous basic or acidic conditions. Minimize exposure to humid air during weighing. Work under inert atmosphere (N₂ or Ar) when moisture sensitivity is critical.
- Solubility: The hydrochloride salt is typically soluble in water and polar protic solvents such as methanol. Solubility in nonpolar organic solvents is limited.
- Safety: Follow standard laboratory safety practices. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.
Purity, Specifications, and Quality Assurance
Research-grade (S)-α-Amino-γ-butyrolactone hydrochloride from Aladdin Scientific (SKU: A101211) is characterized by its defined enantiomeric configuration and controlled purity suitable for demanding synthetic applications. Specific purity values, enantiomeric excess (ee), and analytical data are provided on the product Certificate of Analysis (COA) accompanying each lot. Researchers are encouraged to verify the following parameters upon receipt:
- Appearance and physical form (typically white to off-white solid)
- Purity by HPLC or titration
- Enantiomeric excess (ee) confirmed by chiral HPLC or optical rotation
- Water content (Karl Fischer titration, where applicable)
Contact Aladdin Scientific technical support for lot-specific COA documents or custom purity requirements.
Frequently asked questions
What is (S)-α-Amino-γ-butyrolactone hydrochloride used for in the laboratory?
(S)-α-Amino-γ-butyrolactone hydrochloride is primarily used as a chiral building block in asymmetric synthesis and peptide chemistry. Its reactive γ-lactone ring can be selectively opened by nucleophiles such as amines, thiols, and alcohols, enabling the preparation of diverse amino acid scaffolds and homoserine-derived natural product analogues.
How should (S)-α-Amino-γ-butyrolactone hydrochloride be stored to maintain stability?
The compound should be stored in a tightly sealed container under cool, dry conditions away from moisture and light; refrigerated storage at 2–8 °C is generally recommended. Because the lactone moiety is susceptible to hydrolysis, exposure to humid air or aqueous media should be minimized. Always consult the Certificate of Analysis for lot-specific storage instructions.
What is the significance of the S-configuration in this compound?
The S-configuration at the α-carbon defines a single enantiomer, which is critical for applications requiring stereospecific reactivity or the synthesis of enantiomerically pure targets. Using a single-enantiomer starting material helps avoid racemic mixtures in downstream products and is especially important in pharmaceutical and agrochemical research where chirality influences biological activity.
Is (S)-α-Amino-γ-butyrolactone hydrochloride related to homoserine lactone?
Yes. (S)-α-Amino-γ-butyrolactone hydrochloride is structurally equivalent to L-homoserine lactone hydrochloride, as both describe the cyclic lactone formed by intramolecular esterification of L-homoserine. This relationship makes the compound relevant to the study and synthesis of N-acyl homoserine lactone (AHL) quorum-sensing signals, though the free amine compound itself is an unacylated precursor or analogue.
What solvents are suitable for dissolving (S)-α-Amino-γ-butyrolactone hydrochloride?
As a hydrochloride salt, the compound is typically soluble in water and polar protic solvents such as methanol and ethanol. Solubility in aprotic polar solvents such as DMSO may also be possible. Solubility in nonpolar solvents such as diethyl ether, hexane, or toluene is expected to be low. Always perform a small-scale solubility test before preparing large working solutions.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for lactone reactivity and amino acid chemistry.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. General reference for stereochemistry and chiral building blocks.
- Fuqua, W. C.; Winans, S. C.; Greenberg, E. P. Quorum sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulators. J. Bacteriol. 1994, 176, 269–275. Background reference for homoserine lactone quorum sensing relevance. doi:10.1128/jb.176.2.269-275.1994
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）