Bacillomycin

Bacillomycins are a group of antifungal polypeptide antibiotics isolated from Bacillus subtilis.

Bacillomycin D
Names
IUPAC name
3-[3,9-Bis(2-amino-2-oxo-ethyl)-16-(1-hydroxyethyl)-19-(hydroxymethyl)-6-[(4-hydroxyphenyl)methyl]-13-octyl-2,5,8,11,15,18,21,24-octaoxo-1,4,7,10,14,17,20,23-octazabicyclo[23.3.0]octacosan-22-yl]propanoic acid
Systematic IUPAC name
3-[16,22-Bis(carbamoylmethyl)-9-(1-hydroxyethyl)-6-(hydroxymethyl)-19-[(4-hydroxyphenyl)methyl]-12-octyl-1,4,7,10,14,17,20,23-octaoxo-hexacosahydro-1H-pyrrolo[1,2-j]1,4,7,10,13,16,19,22-octaazacyclopentacosan-3-yl]propanoic acid
Other names
3-[16,22-bis(carbamoylmethyl)-9-(1-hydroxyethyl)-6-(hydroxymethyl)-19-[(4-hydroxyphenyl)methyl]-12-octyl-1,4,7,10,14,17,20,23-octaoxo-octadecahydro-2H-pyrrolo[1,2-j]1,4,7,10,13,16,19,22-octaazacyclopentacosan-3-yl]propanoic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C45H68N10O15/c1-3-4-5-6-7-8-10-26-20-36(61)49-30(21-34(46)59)41(66)51-29(19-25-12-14-27(58)15-13-25)40(65)52-31(22-35(47)60)45(70)55-18-9-11-33(55)43(68)50-28(16-17-37(62)63)39(64)53-32(23-56)42(67)54-38(24(2)57)44(69)48-26/h12-15,24,26,28-33,38,56-58H,3-11,16-23H2,1-2H3,(H2,46,59)(H2,47,60)(H,48,69)(H,49,61)(H,50,68)(H,51,66)(H,52,65)(H,53,64)(H,54,67)(H,62,63) ☒N
    Key: VLKSXJAPRDAENT-UHFFFAOYSA-N ☒N
  • CCCCCCCCC1CC(=O)NC(CC(N)=O)C(=O)NC(CC2=CC=C(O)C=C2)C(=O)NC(CC(N)=O)C(=O)N2CCCC2C(=O)NC(CCC(O)=O)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)N1
Properties
C45H68N10O15
Molar mass 989.094 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Examples include:

  • Bacillomycin A (fungosin, structure unknown)[1][2]
  • Bacillomycin C (structure unknown)[2]
  • Bacillomycin D (C45H68N10O15)[3]
  • Bacillomycin F (C52H84N12O14)[4]
  • Bacillomycin Fc (C52H84N12O14)[5]
  • Bacillomycin L (Landy substance)[2][6]
  • Bacillomycin S (structure unknown)[2]

References
  1. Bacillomycin A
  2. John Buckingham (ed.). Dictionary of Natural Products. pp. 590–591.
  3. Peypoux, F; Besson, F; Michel, G; Delcambe, L (1981). "Structure of bacillomycin D, a new antibiotic of the iturin group". European Journal of Biochemistry. 118 (2): 323–7. doi:10.1111/j.1432-1033.1981.tb06405.x. PMID 7285926.
  4. CID 3086138 from PubChem
  5. CID 3086563 from PubChem
  6. Zhang, B; Dong, C; Shang, Q; Cong, Y; Kong, W; Li, P (2013). "Purification and partial characterization of bacillomycin L produced by Bacillus amyloliquefaciens K103 from lemon". Applied Biochemistry and Biotechnology. 171 (8): 2262–72. doi:10.1007/s12010-013-0424-7. PMID 24043450. S2CID 9380325.


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