Gladiolin

Gladiolin is a polyketide natural product produced by Burkholderia gladioli BCC0238 which is isolated from sputum of cystic fibrosis patients. It was found to be a novel macrolide antibiotic which presented an activity against Mycobacterium tuberculosis. Gladiolin is structurally much more stable than its analogue etnangien as an efficient myxobacterial RNA polymerase inhibitor due to the lack of highly labile hexaene moiety in gladiolin. The good activity and high stability of gladiolin offers it the potential for further development as an antibiotic against antibiotic-resistant M. tuberculosis.

Gladiolin
Names
IUPAC name
(8E,10E,14E,16R,17R)-6-Hydroxy-4,14,16-trimethyl-17-[(2S,4R,8S,10Z,12E,15S,16S,18R,19S,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,19-dimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]octadeca-8,10,14-trienoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C45H76O10/c1-31(18-13-9-8-10-15-20-37(46)27-32(2)24-25-44(51)52)26-34(4)35(5)43-28-38(47)21-17-23-39(54-7)22-16-12-11-14-19-33(3)40(48)29-41(49)36(6)42(50)30-45(53)55-43/h8-12,14-16,26,32-43,46-50H,13,17-25,27-30H2,1-7H3,(H,51,52)/b9-8+,14-11+,15-10+,16-12-,31-26+/t32?,33-,34+,35+,36-,37?,38+,39+,40-,41+,42+,43-/m0/s1
    Key: QOJUVWWXRXLGFG-WIDAHPLTSA-N
SMILES
  • C[C@H]1C/C=C/C=C\C[C@H](CCC[C@H](C[C@H](OC(=O)C[C@H]([C@H]([C@@H](C[C@@H]1O)O)C)O)[C@H](C)[C@H](C)/C=C(\C)/CC/C=C/C=C/CC(CC(C)CCC(=O)O)O)O)OC
Properties
C44H74O11
Molar mass 779.065 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.