Chemical variation from the neoantimycin depsipeptide assembly line.
Here we report the biosynthetic pathway for the neoantimycin and present three novel neoantimycin analogues, neoantimycin D (1), E (2) and F (3), from this assembly system from Streptoverticillium orinoci. Identification of these novel neoantimycin variants was achieved by selective MS/MS interrogation of natural product extracts using diagnostic fragments of the known neoantimycins. Their structures, including the absolute configurations, were elucidated using a combination of NMR experiments, detailed MS/MS experiments and the advanced Marfey's method. The biosynthetic pathway of neoantimycin was dissected by genome sequencing data analysis for the first time, which includes a hybrid nonribosomal peptide synthetase (NRPS) and polyketide synthetase (PKS) assembly lines.
Department of Biochemistry and Biomedical Sciences, MG DeGroote Institute for Infectious Disease Research, McMaster University, Hamilton, Ontario, Canada.
Xiang
X
Li
Rostyslav
R
Zvanych
Stephanie A
SA
Vanner
Wenliang
W
Wang
Nathan A
NA
Magarvey
D047630:Depsipeptides / Q000096:biosynthesis* / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000378:metabolism; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D053719:Tandem Mass Spectrometry
D047630:Depsipeptides; D009930:Organic Chemicals; C002699:neoantimycin
Biosynthesis GRP-78; Depsipeptide; Neoantimycin; Streptoverticillium orinoci