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	150999-05-6  Y
PubChem CID	6438888
ChemSpider	4943331
UNII	YYZ37B8VCV
CompTox Dashboard (EPA)	DTXSID701031592
Chemical and physical data
Formula	C30H48N2O4
Molar mass	500.724 g·mol−1
3D model (JSmol)	Interactive image
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.