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Description
TCI E1444 with CAS number 946511-97-3 is 2-Ethylbutyl L-Alaninate Hydrochloride, the hydrochloride salt of an L-alanine ester formed with the branched alcohol 2-ethylbutanol. The compound is a very well-recognised molecular building block in phosphoramidate prodrug chemistry, the approach commonly referred to as ProTide technology, in which an amino acid ester is attached to a phosphorus centre in order to improve the absorption and intracellular activation of antiviral compounds. Its role in the laboratory is to supply a chiral amino acid ester fragment in a stable salt form, ready to be coupled at the phosphorus-linking stage.
The property that makes this material the preferred choice is its hydrochloride salt form. Free amino acid esters tend to be unstable and readily undergo cyclisation to diketopiperazines, whereas the salt form locks the amine group in a protonated state so that the material can be weighed, stored, and handled far more easily. The L configuration at the alanine stereocentre is preserved, which is decisive because the stereochemistry of this fragment has a direct bearing on the enzymatic activation of the resulting prodrug. The branched 2-ethylbutyl chain confers greater lipophilicity than shorter, straight-chain esters.
In Indonesian laboratories this type of reagent is used mainly in medicinal chemistry and synthetic organic research groups working on nucleoside and nucleotide analogues, in university and institutional research facilities, and in pharmaceutical development units exploring prodrug strategies. Because it is a defined chiral building block delivered as a handling-friendly salt, it suits multistep synthesis work where consistency between batches matters and where researchers need a reliable starting fragment rather than one prepared in-house.
Laboratory Applications
Phosphoramidate (ProTide) prodrug synthesis: it supplies the amino acid ester portion that is coupled to a phosphorus centre, which is the defining structural step in this prodrug design approach.
Nucleoside and nucleotide analogue research: the fragment is attached to nucleoside phosphate derivatives to improve cellular uptake, a strategy widely applied in antiviral compound development programmes.
Chiral building block in multistep organic synthesis: the preserved L configuration at the alanine centre lets researchers carry defined stereochemistry through a synthetic sequence without a separate resolution step.
Structure–activity relationship studies on ester chain variation: the branched 2-ethylbutyl group gives greater lipophilicity than shorter straight-chain esters, making it useful for comparative series work.
Medicinal chemistry method development: as a stable, weighable hydrochloride salt it serves as a dependable reference substrate when optimising coupling conditions, reagents, and reaction workup procedures.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS number: 946511-97-3
Chemical name: 2-Ethylbutyl L-Alaninate Hydrochloride
Category: Chemistry > Chemical Biology > Peptide Chemistry
Product code: E1444
Pack sizes: available in standard TCI research-scale packaging; please confirm the size options when ordering
Storage: store under the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the material in its original tightly closed container, kept in a cool, dry, and well-ventilated place away from moisture, since amino acid ester hydrochlorides are generally sensitive to humidity. Glass containers with tight-fitting closures are suitable, and the container should be resealed promptly after each use; weighing under reduced exposure to ambient air helps preserve quality. Handle the compound in a fume hood using standard personal protective equipment, including safety glasses, gloves, and a laboratory coat, and avoid inhalation of dust or direct contact with skin and eyes. Keep the product separate from strong bases and strong oxidising agents. Always consult the manufacturer's safety data sheet for the specific storage temperature, hazard classification, and disposal requirements before use.
