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Mycosubtilin

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Mycosubtilin
Names
IUPAC name
3-[(3R,6R,9R,12R,15S,22S,25S,30aS)-6,9,15,22-Tetrakis(2-amino-2-oxoethyl)-3-(4-hydroxybenzyl)-12-(hydroxymethyl)-18-(11-methyltridecyl)-1,4,7,10,13,16,20,23,26-nonaoxotriacontahydropyrrolo[1,2-g] [1,4,7,10,13,16,19,22,25]nonaazacyclooctacosin-25-yl]propanamide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C55H86N14O16/c1-3-30(2)13-10-8-6-4-5-7-9-11-14-32-24-47(77)62-36(25-43(57)73)50(80)63-34(20-21-42(56)72)55(85)69-22-12-15-41(69)54(84)67-35(23-31-16-18-33(71)19-17-31)49(79)64-38(27-45(59)75)51(81)65-39(28-46(60)76)52(82)68-40(29-70)53(83)66-37(26-44(58)74)48(78)61-32/h16-19,30,32,34-41,70-71H,3-15,20-29H2,1-2H3,(H2,56,72)(H2,57,73)(H2,58,74)(H2,59,75)(H2,60,76)(H,61,78)(H,62,77)(H,63,80)(H,64,79)(H,65,81)(H,66,83)(H,67,84)(H,68,82)/t30?,32?,34-,35+,36-,37-,38+,39+,40+,41-/m0/s1
    Key: RCIPRGNHNAEGHR-ZLHAWHIKSA-N
  • InChI=1/C55H86N14O16/c1-3-30(2)13-10-8-6-4-5-7-9-11-14-32-24-47(77)62-36(25-43(57)73)50(80)63-34(20-21-42(56)72)55(85)69-22-12-15-41(69)54(84)67-35(23-31-16-18-33(71)19-17-31)49(79)64-38(27-45(59)75)51(81)65-39(28-46(60)76)52(82)68-40(29-70)53(83)66-37(26-44(58)74)48(78)61-32/h16-19,30,32,34-41,70-71H,3-15,20-29H2,1-2H3,(H2,56,72)(H2,57,73)(H2,58,74)(H2,59,75)(H2,60,76)(H,61,78)(H,62,77)(H,63,80)(H,64,79)(H,65,81)(H,66,83)(H,67,84)(H,68,82)/t30?,32?,34-,35+,36-,37-,38+,39+,40+,41-/m0/s1
    Key: RCIPRGNHNAEGHR-ZLHAWHIKBU
  • CCC(C)CCCCCCCCCCC1CC(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)CO)CC(=O)N)CC(=O)N)Cc3ccc(cc3)O)CCC(=O)N)CC(=O)N
Properties
C55H86N14O16
Molar mass 1199.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mycosubtilin is a natural lipopeptide with antifungal and hemolytic activities and isolated from Bacillus species. It belongs to the iturin lipopeptide family.

Definition

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Mycosubtilin is a natural lipopeptide. It is produced by the strains of Bacillus spp mainly by Bacillus subtilis. It was discovered due to its antifungal activities.[1] It belongs to the family of iturin lipopeptides[2]

Structure

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Mycosubtilin is a heptapeptide, cyclized in a ring with a β-amino fatty acid.[3] The peptide sequence is composed of L-Asn-D-Tyr-D-Asn-L-Gln-L-Pro-D-Ser-L-Asn.[4]

Biological activities

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Mycosubtilin has strong antifungal and hemolytic activities.[5][6] It is active against fungi and yeasts such as Candida albicans, Candida tropicalis, Saccharomyces cerevisiae, Penicillium notatum, and Fusarium oxysporum.[7][8][9]

Its antibacterial activity is quite limited to bacteria such as Micrococcus luteus.[10]

See also

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References

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  1. ^ Walton R.B. & Woodruff H.B., 1949. A crystalline antifungal agent, mycosubtilin, isolated from subtilin broth. J. Clin. Invest., 28, 924-926.
  2. ^ Mehmet Nail Nasir, Françoise Besson & Magali Deleu, «Interactions des antibiotiques ituriniques avec la membrane plasmique. Apport des systèmes biomimétiques des membranes (synthèse bibliographique)», Base [En ligne], numéro 3, Volume 17 (2013), 505-516 URL : http://popups.ulg.ac.be/1780-4507/index.php?id=10280.
  3. ^ Nasir M.N. & Besson F., 2011. Specific interactions of mycosubtilin with cholesterol-containing artificial membranes. Langmuir, 27, 10785-10792.
  4. ^ Peypoux F. et al., 1986. Revised structure of mycosubtilin, a peptidolipid antibiotic from Bacillus subtilis. J. Antibiot., 39, 636-641.
  5. ^ Besson F., Peypoux F., Michel G. & Delcambe L., 1979. Antifungal activity upon Saccharomyces cerevisiae of iturin A, mycosubtilin, bacillomycin L and of their derivatives; inhibition of this antifungal activity by lipid antagonists. J. Antibiot., 32, 828-833.
  6. ^ Thimon L. et al., 1992. Interactions of bioactive lipopeptides, iturin A and surfactin from Bacillus subtilis. Biotechnol. Appl. Biochem., 16, 144-151.
  7. ^ Hourdou M.L. & Besson F., 1994. Surfactine et antibiotiques ituriniques : structure, propriétés et biosynthèse des lipopeptides de Bacillus subtilis. Regard Biochim., 1, 35-42.
  8. ^ Besson F., Peypoux F., Michel G. & Delcambe L., 1979a Antifungal activity upon Saccharomyces cerevisiae of iturin A, mycosubtilin, bacillomycin L and of their derivatives; inhibition of this antifungal activity by lipid antagonists. J. Antibiot., 32, 828-833
  9. ^ Besson F. & Michel G., 1989. Action of mycosubtilin, an antifungal antibiotic of Bacillus subtilis, on the cell membrane of Saccharomyces cerevisiae. Microbios, 59, 113-121.
  10. ^ Besson F., Peypoux F. & Michel G., 1978b. Action of mycosubtilin and of bacillomycin L on Micrococcus luteus cells and protoplasts: influence of the polarity of the antibiotics upon their action on the bacterial cytoplasmic membrane. FEBS Lett., 90, 36-40.
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