New Lactimidomycin Congeners Shed Insight into Lactimidomycin Biosynthesis in Streptomyces amphibiosporus

Lactimidomycin (LTM, 1) is a macrolide antitumor antibiotic with a glutarimide side chain from Streptomyces amphibiosporus ATCC53964. To further develop LTM and related analogues as drug candidates we have (i) improved LTM production by ∼20 fold, (ii) identified three new metabolites (2−4) possibly...

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Bibliographic Details
Published in:Organic letters 2007-12, Vol.9 (25), p.5183-5186
Main Authors: Ju, Jianhua, Seo, Jeong-Woo, Her, Yeng, Lim, Si-Kyu, Shen, Ben
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Chromatography, High Pressure Liquid
Macrolides - chemistry
Macrolides - metabolism
Molecular Structure
Piperidones - chemistry
Piperidones - metabolism
Streptomyces - chemistry
Streptomyces - metabolism
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Summary:Lactimidomycin (LTM, 1) is a macrolide antitumor antibiotic with a glutarimide side chain from Streptomyces amphibiosporus ATCC53964. To further develop LTM and related analogues as drug candidates we have (i) improved LTM production by ∼20 fold, (ii) identified three new metabolites (2−4) possibly involved in the LTM biosynthetic pathway; (iii) found 3 to be identical with a previously identified isomigrastatin precursor, (iv) determined the absolute stereochemistry of LTM, and (v) produced new LTM rearrangement products 2a−d and 4a−d.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702249g