pulcherriminic acid

Names

[ CAS No. ]:
957-86-8

[ Name ]:
pulcherriminic acid

[Synonym ]:
3,6-diisobutylpyrazine-2,5-diol 1,4-dioxide
1,5-dihydroxy-3,6-bis(2-methylpropyl)-4-oxidopyrazin-4-ium-2-one
Pulcherriminic acid
2,5-Diisobutyl-3,6-dihydroxy-pyrazine-1,4-dioxide

Biological Activity

[Description]:

Pulcherriminic acid is a cyclic dipeptide antimicrobial agent with high affinity for Fe3+, found mainly in Bacillus and yeast. Pulcherriminic acid chelates iron ions through a non-enzymatic reaction to form the extracellular red pigment pulcherrimin, which competes for iron nutrition and thus achieves an antibacterial effect. Pulcherriminic acid has great applications in food, agriculture and medical industries[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Pulcherriminic acid can inhibit the formation of Bacillus subtilis biofilm[2]. Pulcherriminic acid can form insoluble red pigment pulcherrimin in the presence of Fe3+ to compete for iron nutrients, thereby inhibiting the growth of Metschnikowia yeasts[3].

[References]

[1]. Siqi Yuan, et al. Research Progress of the Biosynthesis of Natural Bio-Antibacterial Agent Pulcherriminic Acid in Bacillus. Molecules. 2020 Nov 28;25(23):5611.

[2]. Sofia Arnaouteli, et al. Pulcherrimin formation controls growth arrest of the Bacillus subtilis biofilm. Proc Natl Acad Sci U S A. 2019 Jul 2;116(27):13553-13562

[3]. Vytautas Melvydas, et al. In vitro inhibition of Saccharomyces cerevisiae growth by Metschnikowia spp. triggered by fast removal of iron via two ways. Braz J Microbiol. 2020 Dec;51(4):1953-1964. doi: 10.1007/s42770-020-00357-3. Epub 2020 Aug 11.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₂H₂₀N₂O₄

[ Molecular Weight ]:
256.29800

[ Exact Mass ]:
256.14200

[ PSA ]:
87.92000

[ LogP ]:
1.61670

Safety Information

[ HS Code ]:
2933599090

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%