N-Acetyl-3-(2,6-difluorophenyl)-D-alanine: Key Facts & FAQs

N-Acetyl-3-(2,6-difluorophenyl)-D-alanine is a fluorinated, N-acetyl-protected unnatural D-amino acid used as a synthetic building block in medicinal chemistry, peptide research, and pharmaceutical development.

Chemical Name

N-Acetyl-3-(2,6-difluorophenyl)-D-alanine

Compound Class

N-acetyl protected unnatural D-amino acid with an aryl fluorine substituent

Stereochemistry

D-configuration at the alpha carbon

Key Structural Feature

2,6-difluorophenyl group at the beta position; N-acetyl protecting group on the amine

Typical Application

Synthetic building block for peptide synthesis, medicinal chemistry, and pharmaceutical research

Supplier SKU

N731612 (Aladdin Scientific)

What Is N-Acetyl-3-(2,6-difluorophenyl)-D-alanine?

N-Acetyl-3-(2,6-difluorophenyl)-D-alanine is a non-proteinogenic, fluorinated amino acid derivative belonging to the class of unnatural D-amino acids. Its structure consists of a D-alanine backbone in which the beta carbon bears a 2,6-difluorophenyl aryl group, and the alpha-amino group is protected with an acetyl moiety.

The incorporation of two fluorine atoms at the 2- and 6-positions of the phenyl ring imparts distinctive electronic and steric properties. Fluorine substitution is widely used in medicinal chemistry to modulate metabolic stability, lipophilicity, membrane permeability, and binding affinity of drug candidates.

The N-acetyl group serves as a protecting group for the amine functionality, making this compound a versatile intermediate for further synthetic transformations in the preparation of peptide-based drugs, enzyme inhibitors, and other bioactive molecules.

Structural and Chemical Properties

The 2,6-difluorophenyl substitution pattern creates a sterically hindered aromatic ring. The two ortho-fluorine atoms restrict rotation around the phenyl–methylene bond, which can influence the conformational preferences of derived peptides and peptidomimetics.

Fluorine atoms are strongly electron-withdrawing via induction, altering the pKa of neighboring functional groups and affecting the overall polarity of the molecule. These properties are routinely exploited to fine-tune the pharmacokinetic and pharmacodynamic profiles of fluorinated drug candidates.

The D-stereochemistry at the alpha carbon provides resistance to proteolytic degradation by most naturally occurring L-amino-acid-specific proteases, which can be advantageous in the design of metabolically stable peptides and peptidomimetics for in vivo applications.

Handling, Storage, and Safety Considerations

As with most fine chemical research reagents, N-Acetyl-3-(2,6-difluorophenyl)-D-alanine should be handled in a well-ventilated laboratory environment, with standard personal protective equipment including gloves, lab coat, and eye protection.

For optimal stability, the compound should be stored in a tightly sealed container, protected from moisture and light, at the temperature specified on the product label or certificate of analysis. Researchers should consult the Safety Data Sheet (SDS) provided with each shipment for specific hazard classification and first-aid measures.

Avoid contact with strong oxidizers or strong bases that may hydrolyze the acetyl protecting group. If the compound is dissolved in solution, prepare working stocks fresh or verify stability under specific solvent conditions prior to use in sensitive assays.

Ordering and Specifications at Aladdin Scientific

N-Acetyl-3-(2,6-difluorophenyl)-D-alanine is available from Aladdin Scientific under SKU N731612. Researchers and procurement teams can place orders directly through the Aladdin Scientific website or by contacting the sales team for bulk quantities or custom packaging requirements.

Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity and purity determined by standard analytical methods. Researchers requiring specific purity grades, custom quantities, or technical documentation should contact Aladdin Scientific's technical support team prior to ordering.

For questions regarding payment options, promotions, shipping timelines, or return policies, please refer to the relevant sections of the Aladdin Scientific website or reach out to customer service directly.

Frequently asked questions

What is N-Acetyl-3-(2,6-difluorophenyl)-D-alanine used for?

N-Acetyl-3-(2,6-difluorophenyl)-D-alanine is primarily used as a synthetic building block in medicinal chemistry and peptide research. Its fluorinated aryl side chain and N-acetyl protecting group make it a versatile intermediate for preparing unnatural peptides, peptidomimetics, and fluorine-containing pharmaceutical candidates. Researchers also use it to study the impact of fluorine substitution on peptide conformation and biological activity.

Why is the D-configuration important for this compound?

The D-configuration at the alpha carbon of this amino acid derivative confers resistance to proteolytic enzymes that are highly selective for L-amino acids, the natural configuration found in proteins. This stereochemical feature makes D-amino acid-containing peptides more metabolically stable in biological environments compared to their all-L counterparts. This property is particularly valuable in drug development, where prolonged in vivo half-life is desirable.

What role do the two fluorine atoms play in the 2,6-difluorophenyl group?

The two fluorine atoms at the 2- and 6-positions of the phenyl ring introduce steric bulk at both ortho positions, restricting conformational freedom and influencing the spatial orientation of the aryl group within derived structures. Additionally, fluorine is strongly electronegative and electron-withdrawing by induction, which can alter the electronic properties of the aromatic ring and nearby functional groups. These combined effects are commonly leveraged in medicinal chemistry to improve metabolic stability, binding selectivity, and membrane permeability of drug candidates.

How should I store N-Acetyl-3-(2,6-difluorophenyl)-D-alanine to maintain its integrity?

The compound should be stored in a tightly sealed container, away from moisture, light, and incompatible materials such as strong oxidizers and strong bases. Please refer to the product label and the accompanying Certificate of Analysis (CoA) for the recommended storage temperature. For extended storage, keeping the compound under the conditions specified in the CoA will help maintain chemical integrity.

How do I order N-Acetyl-3-(2,6-difluorophenyl)-D-alanine from Aladdin Scientific?

You can order N-Acetyl-3-(2,6-difluorophenyl)-D-alanine directly from the Aladdin Scientific website using SKU N731612. For bulk orders, custom quantities, or additional technical information, contact the Aladdin Scientific sales or technical support team. Multiple payment options and delivery terms are available as described on the Aladdin website.

References

1. Fluorine in medicinal chemistry: general principles and recent advances. (Textbook-level reference; specific citation not provided in source material.)
2. D-Amino acids in biological systems and drug design. (Textbook-level reference; specific citation not provided in source material.)
3. Aladdin Scientific product page: N-Acetyl-3-(2,6-difluorophenyl)-D-alanine, SKU N731612.

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