1-Benzyl D-Aspartate: Properties, Uses & FAQs

1-Benzyl D-Aspartate is a selectively protected derivative of D-aspartic acid in which the alpha-carboxyl group is esterified with a benzyl group, serving as a versatile building block in asymmetric synthesis and peptide chemistry research.

Product SKU

B152657

Chemical Name

1-Benzyl D-Aspartate

Compound Class

Protected D-amino acid (benzyl ester derivative)

Stereochemistry

D-configuration at the alpha carbon

Primary Application

Building block in peptide synthesis and organic synthesis

Protecting Group Removal

Benzyl ester removable by hydrogenolysis (Pd/C, H2) or acidolysis

What Is 1-Benzyl D-Aspartate?

1-Benzyl D-Aspartate is the 1-position (alpha-carboxyl) benzyl ester of D-aspartic acid, a non-proteinogenic D-form amino acid. By selectively protecting the alpha-carboxylate as a benzyl ester, the compound leaves the side-chain beta-carboxylic acid and the alpha-amine available for further functionalization. This selectivity makes it a valuable chiral synthon in both solution-phase and solid-phase peptide synthesis, as well as in the preparation of peptidomimetics and other nitrogen-containing heterocycles.

The compound belongs to the broader class of protected amino acid building blocks routinely used in research laboratories to introduce D-amino acid residues into peptide sequences with defined stereochemistry.

Key Chemical Properties and Handling

1-Benzyl D-Aspartate contains two carboxylic acid functionalities and one primary amine, giving it amphoteric character. The benzyl ester at the 1-position is orthogonally removable under hydrogenolytic conditions (e.g., Pd/C under hydrogen atmosphere) or by strong acid treatment, providing flexibility in multi-step synthetic schemes.

As with most amino acid derivatives, the compound should be stored in a cool, dry environment away from moisture and strong oxidizing agents. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before handling. Standard laboratory personal protective equipment (PPE), including gloves, lab coat, and eye protection, is recommended.

Note: Specific physical constants such as melting point, optical rotation, and solubility should be verified against the Certificate of Analysis (CoA) supplied with each lot of B152657, as these values may vary by batch.

Applications in Research

The primary utility of 1-Benzyl D-Aspartate lies in its role as a chiral building block for the construction of D-aspartate-containing peptides. D-Amino acids are increasingly incorporated into therapeutic peptide candidates to confer resistance to proteolytic degradation, thereby improving metabolic stability. Researchers working on enzyme inhibitors, receptor ligands, and antimicrobial peptides may require D-aspartate residues at specific sequence positions.

Beyond peptide synthesis, the compound can serve as a starting material or intermediate in the synthesis of aspartate analogs, beta-lactams, and other pharmacologically relevant scaffolds. Its defined D-stereochemistry is essential for studies examining stereospecific biological interactions.

Quality, Purity and Specifications

Aladdin Scientific supplies 1-Benzyl D-Aspartate (SKU: B152657) as a research-grade reagent. Purity is confirmed by standard analytical methods such as HPLC and NMR. Buyers should request a copy of the Certificate of Analysis (CoA) and the Safety Data Sheet (SDS) at the time of purchase to verify lot-specific purity, appearance, and other quality attributes.

For applications requiring higher stereochemical purity or specific grade materials (e.g., GMP-grade), please contact Aladdin Scientific's technical support team to discuss available options and current stock specifications.

Ordering and Storage Information

1-Benzyl D-Aspartate is available for order under SKU B152657 through the Aladdin Scientific website or by contacting your regional sales representative. Standard packaging and available quantities are listed on the product page; custom quantities may be arranged upon request.

For optimal stability, store the compound according to the conditions specified on the product label and CoA. General best practice for amino acid ester derivatives includes storage at 2–8 °C or as indicated, in a tightly sealed container under inert atmosphere where long-term storage is required. Always verify storage conditions from the official product documentation for each specific lot.

Frequently asked questions

What is 1-Benzyl D-Aspartate used for in research?

1-Benzyl D-Aspartate is primarily used as a selectively protected chiral building block in peptide synthesis, where it allows the incorporation of D-aspartate residues into peptide sequences. It is also employed as a synthetic intermediate for aspartate analogs and other pharmacologically relevant scaffolds requiring defined D-stereochemistry.

How is the benzyl protecting group removed from 1-Benzyl D-Aspartate?

The benzyl ester protecting group can be removed by catalytic hydrogenolysis using palladium on carbon (Pd/C) under a hydrogen atmosphere, which is a mild and selective method compatible with many other functional groups. Acidolytic conditions using strong acids such as HBr/AcOH may also be employed depending on the overall synthetic strategy.

What is the difference between 1-Benzyl D-Aspartate and 4-Benzyl D-Aspartate?

In 1-Benzyl D-Aspartate, the benzyl ester is located at the alpha (1-position) carboxyl group, leaving the beta (4-position) side-chain carboxyl free. In 4-Benzyl D-Aspartate, the reverse protection pattern applies, with the benzyl ester on the side-chain carboxyl. The choice between the two depends on which carboxyl group needs to remain free for coupling or further functionalization in the target synthesis.

What analytical methods confirm the purity of B152657?

Purity of 1-Benzyl D-Aspartate (B152657) is typically confirmed using HPLC for chemical purity and NMR spectroscopy for structural identity. Optical rotation measurement may also be used to verify stereochemical integrity. Lot-specific data are provided in the Certificate of Analysis (CoA) accompanying each shipment.

How should 1-Benzyl D-Aspartate be stored to maintain stability?

General best practice for amino acid benzyl ester derivatives is to store them in a cool, dry environment, typically at 2–8 °C, in a tightly sealed container, and under inert atmosphere for long-term storage. Always refer to the official product label and CoA for lot-specific storage instructions provided by Aladdin Scientific.

References

1. General reference: Bodanszky, M. Principles of Peptide Synthesis. Springer, 1984. (General principles of amino acid protection in peptide synthesis.)
2. Aladdin Scientific Product Page: 1-Benzyl D-Aspartate, SKU B152657. Aladdin Scientific official website.
3. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed. Wiley, 2006. (Reference for benzyl ester protecting group chemistry and removal conditions.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.