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Antibiotic
Mycosubtilin
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Mycosubtilin

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Mycosubtilin
Mycosubtilin.svg
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
PubChem CID
  • 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

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. It belongs to the family of iturin lipopeptides

Structure

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

Biological activities

Mycosubtilin has strong antifungal and hemolytic activities. It is active against fungi and yeasts such as Candida albicans, Candida tropicalis, Saccharomyces cerevisiae, Penicillium notatum, and Fusarium oxysporum.

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


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