Vicenistatin

Vicenistatin
Identifiers
IUPAC name
  • (3E,5E,7S,8S,10E,13E,15E,19S)-7,11,13,19-Tetramethyl-2-oxoazacycloicosa-3,5,10,13,15-pentaen-8-yl 2,4,6-trideoxy-4-(methylamino)-β-D-ribo-hexopyranoside
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC30H48N2O4
Molar mass500.724 g·mol−1
3D model (JSmol)
SMILES
  • C[C@H]1CC/C=C/C=C(/C/C(=C/C[C@@H]([C@H](/C=C/C=C/C(=O)NC1)C)O[C@H]2C[C@@H]([C@@H]([C@H](O2)C)NC)O)/C)\C
InChI
  • InChI=1S/C30H48N2O4/c1-21-12-8-7-9-13-23(3)20-32-28(34)15-11-10-14-24(4)27(17-16-22(2)18-21)36-29-19-26(33)30(31-6)25(5)35-29/h7-8,10-12,14-16,23-27,29-31,33H,9,13,17-20H2,1-6H3,(H,32,34)/b8-7+,14-10+,15-11+,21-12+,22-16+/t23-,24-,25+,26-,27-,29-,30+/m0/s1
  • Key:FINGADBUNZWVLV-KVAOKYIVSA-N

Vicenistatin is a macrolactam antibiotic synthesized by Streptomyces halstedii HC34. It was originally isolated from this bacterium in 1993.[1] It includes the unusual starter unit methylaspartate.[2]

References

  1. ↑ Shindo K, Kamishohara M, Odagawa A, Matsuoka M, Kawai H (July 1993). "Vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic". The Journal of Antibiotics. 46 (7): 1076–81. doi:10.7164/antibiotics.46.1076. PMID 8360102.
  2. ↑ Ogasawara Y, Kakinuma K, Eguchi T (July 2005). "Involvement of glutamate mutase in the biosynthesis of the unique starter unit of the macrolactam polyketide antibiotic vicenistatin". The Journal of Antibiotics. 58 (7): 468–72. doi:10.1038/ja.2005.62. PMID 16161486.
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