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Pneumocandin B0 (CAS 135575-42-7)

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Alternate Names:
(3S)-(4R,5R)-N2-[(10R,12S)-10,12-Dimethyl-1-oxotetradecyl]- 4,5-dihydroxy-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-(4-hydroxyphenyl)-L-threonyl-(3R)-3-hydroxy-L-glutaminyl-3-hydroxy-L-proline (6→1)-Lactam
Application:
Pneumocandin B0 is a potent antifungal and inhibitor of β-(1,3)-D-glucan synthesis
CAS Number:
135575-42-7
Molecular Weight:
1065.2
Molecular Formula:
C50H80N8O17
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Pneumocandin B0 is a naturally occurring echinocandin, a class of lipopeptides known for their role in inhibiting fungal cell wall synthesis. This compound is derived from the fermentation of the fungus Glarea lozoyensis and serves as a crucial starting material for the synthesis of more potent antifungal agents like caspofungin. Pneumocandin B0′s mechanism of action centers on the inhibition of the enzyme β-(1,3)-D-glucan synthase. This enzyme is pivotal for the synthesis of β-glucan, a critical component of the fungal cell wall that provides structural integrity and protection. By inhibiting this enzyme, Pneumocandin B0 disrupts the construction of the fungal cell wall, leading to osmotic instability and eventual cell lysis. In research contexts, this compound has been extensively used to study fungal physiology and the pathogenesis of fungal infections, particularly in understanding how fungi respond to and compensate for cell wall stress. Additionally, the bioactivity of Pneumocandin B0 has facilitated investigations into the genomic and proteomic responses of fungi to cell wall damage, contributing significantly to the field of fungal biology and helping to explain mechanisms of action for a class of compounds that target a fungal-specific pathway. This research is crucial for developing strategies to combat fungal pathogens that are increasingly resistant to conventional treatments.


Pneumocandin B0 (CAS 135575-42-7) References

  1. Determination of the relative and absolute configuration of the dimethylmyristoyl side chain of pneumocandin B0 by asymmetric synthesis.  |  Leonard, WR., et al. 2002. Org Lett. 4: 4201-4. PMID: 12443058
  2. Preparation and evaluation of novel stationary phases for improved chromatographic purification of pneumocandin B0.  |  Welch, CJ., et al. 2006. J Chromatogr A. 1101: 204-13. PMID: 16257000
  3. Synthesis of the antifungal beta-1,3-glucan synthase inhibitor CANCIDAS (caspofungin acetate) from pneumocandin B0.  |  Leonard, WR., et al. 2007. J Org Chem. 72: 2335-43. PMID: 17343416
  4. Genomics-driven discovery of the pneumocandin biosynthetic gene cluster in the fungus Glarea lozoyensis.  |  Chen, L., et al. 2013. BMC Genomics. 14: 339. PMID: 23688303
  5. Discovery and development of first in class antifungal caspofungin (CANCIDAS®)--a case study.  |  Balkovec, JM., et al. 2014. Nat Prod Rep. 31: 15-34. PMID: 24270605
  6. Engineering of Glarea lozoyensis for exclusive production of the pneumocandin B0 precursor of the antifungal drug caspofungin acetate.  |  Chen, L., et al. 2015. Appl Environ Microbiol. 81: 1550-8. PMID: 25527531
  7. Pneumocandin B0-imprinted Polymer Using Surface-imprinting Technique for Efficient Purification of Crude Product.  |  Zhang, L., et al. 2016. Anal Sci. 32: 923-30. PMID: 27682395
  8. Enhancement of Pneumocandin B0 Production in Glarea lozoyensis by Low-Temperature Adaptive Laboratory Evolution.  |  Song, P., et al. 2018. Front Microbiol. 9: 2788. PMID: 30519220
  9. Effect of fatty acids on intracellular pneumocandin B0 storage in the fermentation of Glarea lozoyensis.  |  Zhang, W., et al. 2023. Bioresour Bioprocess. 10: 63. PMID: 38647938
  10. Use of beta-1,3-glucan-specific antibody to study the cyst wall of Pneumocystis carinii and effects of pneumocandin B0 analog L-733,560.  |  Nollstadt, KH., et al. 1994. Antimicrob Agents Chemother. 38: 2258-65. PMID: 7840554

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Pneumocandin B0, 2 mg

sc-362036
2 mg
$260.00