Product name: N-Benzoyl-(2R,3S)-3-phenylisoserine
Synonym name: (2R,3S)-N-Benzoyl-3-phenylisoserine
Catalogue No.: BP4345
Cas No.: 132201-33-3
Formula: C₁₆H₁₅NO₄
Mol Weight: 285.299
Botanical Source:
Type of Compound:

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams
Inquire for bulk scale.

For Reference Standard and R&D, Not for Human Use Directly.

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

As antimicrobial drug resistance intensifies, finding new, efficient, and safe natural antibacterial products has become an important direction for modern drug development. N-benzoyl-(2R,3S)-3-phenylisoserine (N-Benzoyl-(2R,3S)-3-phenylisoserine), a natural product derivative with a unique structure, has attracted widespread attention in recent years due to its remarkable antibacterial activity and excellent druggability parameters. This compound not only exhibits inhibitory effects on multiple bacterial targets, but also exhibits low toxicity risk and excellent pharmacokinetic profiles, indicating potential as a candidate molecule for next-generation antimicrobial drugs.

This paper aims to systematically review the chemical structure, physicochemical properties, plant origin, and extraction methods of N-benzoyl-(2R,3S)-3-phenylisoserine, explore its pharmacological activity and mechanism of action in depth, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects, aiming to provide comprehensive reference materials for researchers in related fields.

Chemical structure and physicochemical properties

N-benzoyl-(2R,3S)-3-phenylisoserine is an amino acid derivative modified with benzoyl groups, molecular formula C16H15NO4, and molecular weight 285.2990. Its structural features include a benzoyl group serving as an N-terminal protective group, attached to a 3-phenylisserine backbone with two stereocenters, forming a configuration of (2R,3S). The phenyl side chain in this molecule increases its hydrophobicity and aromaticity, facilitating binding to hydrophobic pockets of protein targets.

In terms of physicochemical properties, the LogP value of N-benzoyl-(2R,3S)-3-phenylisoserine is 1.6291, indicating moderate lipid solubility, which facilitates cell membrane penetration while avoiding reduced bioavailability caused by excessive lipid solubility. Its topological pole surface area (TPSA) is 86.63 Ų, indicating that the molecule has certain polarity, which helps with water solubility and polar interaction with the target. The water solubility index was 2.0467, indicating moderate solubility in the aqueous phase, which is beneficial for oral drug absorption. This compound has a relatively low blood-brain barrier penetration ability, suggesting a lower risk of side effects in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenicity test result was 0.0, indicating its non-mutagenic nature and relatively high safety.

Plant Origins and Extraction Methods

Currently, N-benzoyl-(2R,3S)-3-phenylisoserine is mainly isolated from specific Chinese medicinal plants. Related reports indicate that this compound can be detected in certain plants rich in phenylamino acid derivatives, such as the rhizomes or leaves of certain Solanaceae or legume species. Specific plant species and their distribution still require further systematic research.

The extraction method typically uses solvent extraction combined with chromatography separation technology. Common extraction solvents include methanol, ethanol, or their aqueous solutions, which are extracted using ultrasound-assisted or reflux extraction to improve yield. After the extract is liquid-liquid distribution to remove lipophilic impurities, it is purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC). The purified compounds undergo structural identification and purity confirmation using mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR).

With the development of synthetic methods, the chemical synthesis route for N-benzoyl-(2R,3S)-3-phenylisoserine has gradually improved, making large-scale preparation possible and promoting in-depth pharmacological research.

Pharmacological activity research

N-benzoyl-(2R,3S)-3-phenylisserine is a research hotspot due to its remarkable antibacterial activity. In vitro experiments showed that this compound exhibited inhibition against various Gram-positive and Gram-negative bacteria, with particularly strong inhibitory effects against drug-resistant strains. Its minimum inhibitory concentration (MIC) was low micromolar levels across various clinically isolated strains, demonstrating high antibacterial efficacy.

In addition, this compound also has certain inhibitory effects on fungal pathogens, especially by inhibiting key enzymes synthesizing fungal cell membranes, demonstrating broad-spectrum antibacterial potential. Preliminary pharmacodynamic studies in animal models suggest it has good therapeutic effects in treating infectious diseases, with minimal toxic side effects.

The antibacterial activity of N-benzoyl-(2R,3S)-3-phenylisserine is not limited to a single target; its multi-target action makes it more advantageous in inhibiting bacterial growth and resistance mechanisms.

Mechanism of action and molecular targets

The antibacterial mechanism of this compound involves multiple key targets, covering bacterial DNA replication, cell wall synthesis, metabolic pathways, and drug efflux. The main targets include:

• DNA gyrase A (GYRA): As a key enzyme for bacterial DNA replication, inhibition of GYRA leads to abnormal DNA supercoil structures, hindering bacterial proliferation.
• Cell wall synthases (FABI, PENA): inhibit fatty acid biosynthesis and penicillin-binding proteins, interfering with bacterial cell wall synthesis and repair.
• Cell division protein FtsZ (FTSZ): affects bacterial cell division and inhibits bacterial growth.
• Dihydrofolate reductase (DHFR): blocks folic acid metabolism and affects nucleic acid synthesis.
• Fungal-specific targets ERG11 and CYP51A1: Inhibits the synthesis of ergosterol in fungal cell membranes, disrupting membrane integrity.
• Drug efflux pump CDR1: Inhibits drug efflux and enhances intracellular accumulation of antimicrobial drugs.

By coordinating inhibition of these targets, N-benzoyl-(2R,3S)-3-phenylisserine can effectively block the growth and reproduction of bacteria and fungi, reducing the emergence of resistant strains. Furthermore, molecular docking and kinetic simulation studies show that this compound binds stably to target proteins with low binding energy, supporting the molecular basis for multi-target inhibition.

Druggability evaluation and pharmacokinetics

Druggability is an important indicator for evaluating whether candidate molecules for new drugs can enter clinical development. N-benzoyl-(2R,3S)-3-phenylisoserine exhibits excellent druggability parameters:

• The molecular weight (285.2990) complies with the Lipinski rule, which is beneficial for oral absorption.
• LogP (1.6291) is moderate, balancing lipid and water solubility, aiding distribution in the body.
• TPSA (86.63 Ų) is suitable for penetrating cell membranes while ensuring good solubility.
• Water-soluble (2.0467) supports the development of oral formulations.
• Low blood-brain barrier penetration, reducing the risk of central nervous system side effects.
• hERG channel inhibition is negative, indicating a low risk of cardiotoxicity.
• Ames mutagenic test was negative, indicating good safety.

Pharmacokinetic studies show that this compound is well absorbed orally, has a moderate plasma half-life, is widely distributed in the body, but does not easily enter the central nervous system. Metabolism mainly passes through the liver enzyme system, while excretion is primarily via the kidneys. No significant risk of drug interactions, suitable for combination therapy.

Prospects and outlooks for clinical applications

Given the excellent antibacterial activity and good safety observed by N-benzoyl-(2R,3S)-3-phenylisserine in vitro and animal models, it has broad clinical development prospects as a novel antimicrobial drug. Future research should focus on the following aspects:

1. Preclinical toxicology and pharmacodynamic studies: Systematic evaluation of long-term toxicity, immunogenicity, and duration of efficacy.
2. Dosage form development and delivery route optimization: Explore various dosage forms such as oral, injectable, and topical administration to improve bioavailability and patient compliance.
3. Mechanisms of resistance and combination therapy research: In-depth analysis of its mechanisms of action against resistant strains, and evaluation of synergistic effects with existing antimicrobial drugs.
4. Clinical trial design: Design reasonable Phase I to III clinical trials based on existing data to verify their safety and efficacy.

In addition, combining modern drug design technologies, such as computer-aided drug design (CADD), structural optimization, and nanocarrier delivery systems, is expected to further enhance efficacy and safety, promoting early clinical application.

Conclusion

N-benzoyl-(2R,3S)-3-phenylisoserine, as a natural product derivative with multi-target antibacterial activity, demonstrates great potential as a novel antimicrobial drug due to its unique chemical structure and excellent druggability parameters. Its multi-target mechanism not only effectively inhibits the growth of bacteria and fungi but also reduces the risk of drug resistance, meeting the current needs of antimicrobial drug development.

In the future, with further analysis of its pharmacological mechanisms and advancement of preclinical research, N-benzoyl-(2R,3S)-3-phenylisserine is expected to become an important candidate drug in the field of antimicrobial therapy, contributing to the global antimicrobial resistance crisis. Ongoing interdisciplinary collaboration and innovative research will be key to achieving clinical translation.