FR 901379 is an impurity of Micafungin, a lipopeptide compound that acts as an antifungal agent with activity against Aspergillus and Candida species.
CAT No: Z10-101-161
CAS No:144371-88-0
Synonyms/Alias:1-[(4R,5R)-4,5-Dihydroxy-N2-(1-oxohexadecyl)-L-ornithine]-4-[(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonine]pneumocandin A0; (2α,3β,4β)-(4R,5R)-4,5-Dihydroxy-N2-(1-oxohexadecyl)-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonyl-3-hydroxy-L-glutaminyl-3-hydroxy-4-methyl-L-Proline Cyclic (6→1)-Peptide; 1H-Dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine Cyclic Peptide Deriv.
FR 901379 is a naturally derived macrocyclic lactone compound, originally isolated from fungal sources and recognized for its unique structural features and potent biochemical properties. As a member of the macrolide family, it exhibits a distinctive arrangement of functional groups that confer high affinity for specific molecular targets in cellular systems. Its complex architecture and bioactive profile have attracted significant interest from researchers in fields such as chemical biology, microbiology, and natural product chemistry. The compound's ability to modulate biological pathways and its synthetic intractability have made it a valuable tool for probing mechanisms of action and for developing novel research methodologies in the study of macrolide-class natural products.
Antifungal mechanism studies: FR 901379 has been extensively utilized in the investigation of fungal cell wall biosynthesis and integrity. Its selective inhibition of β-1,3-glucan synthase provides a robust experimental model for dissecting the enzymatic steps involved in fungal cell wall formation. Researchers employ this compound to elucidate the molecular interactions that underlie glucan polymerization, facilitating a deeper understanding of antifungal target validation and resistance mechanisms. Experimental use of the molecule has contributed to the identification of critical residues and conformational changes within the target enzyme, advancing the field of antifungal drug discovery.
Natural product biosynthesis research: The unique biosynthetic origin of FR 901379 makes it a valuable reference standard for studies on polyketide synthase and non-ribosomal peptide synthetase pathways. By tracing its biosynthetic intermediates and enzymatic assembly, scientists gain insights into the modular logic of macrolide construction in filamentous fungi. The compound serves as a model substrate for elucidating tailoring reactions, such as macrolactonization and glycosylation, that diversify the structural landscape of natural products. Such research not only enhances our understanding of secondary metabolism but also inspires new strategies for engineered biosynthesis and combinatorial biocatalysis.
Chemical biology probe development: Due to its well-characterized biological activity, FR 901379 is frequently employed as a chemical probe in cellular assays designed to interrogate the function of glucan synthase and related pathways. Its use as a selective inhibitor enables researchers to delineate the roles of specific cell wall components in fungal physiology, stress response, and morphology. Integration of this compound into high-content screening platforms supports the identification of synthetic lethal interactions and compensatory pathways, driving innovation in antifungal research and systems biology.
Analytical method validation: The structural complexity and stability of FR 901379 render it an excellent analytical standard for the development and validation of chromatographic and spectrometric techniques. Laboratories utilize the compound to optimize extraction, separation, and detection protocols in complex biological matrices, ensuring accurate quantification of macrolide-class molecules. Its application in method development extends to quality control and comparative analysis of natural product libraries, supporting reproducibility in research and development workflows.
Lead compound for structure-activity relationship (SAR) studies: The intricate molecular framework of FR 901379 provides a versatile scaffold for SAR investigations aimed at understanding the relationship between structural modifications and biological activity. Medicinal and synthetic chemists employ the molecule as a starting point for the rational design of analogs, systematically altering functional groups to probe the determinants of target affinity and selectivity. These studies are pivotal in guiding the optimization of macrolide derivatives for enhanced potency, stability, and spectrum of activity in research applications.
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