The ansacarbamitocins are a new family of maytansinoids that are unusually substituted with a glucose subunit and two carbamate functional groups and exhibit modest activity against some agricultural fungal disease organisms. Ansacarbamitocins A-F ( 1- 6) all consist of the same macrocyclic core as the ansamitocins, with variation occurring on the glucose unit, while ansacarbamitocins A1 and B1 ( 7, 8) additionally lack the epoxide group on C-4 and C-5.
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Identification of the Bacterial Maytansinoid Gene Cluster Provides Insights into the Post-PKS Modifications of Ansacarbamitocin Biosynthesis.
Org Lett
August 2019
Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences , Shandong University, No. 44 West Wenhua Road , Jinan , Shandong 250012 , P. R. China.
A new biosynthetic gene cluster for the bacterial maytansinoids, ansacarbamitocins (ASCs), was identified in DSM 44262. The post-PKS modifications of ASCs were elucidated on the basis of bioinformatics analysis. Specific gene disruption and heterologous expression led to the isolation of seven new bacterial maytansinoids.
View Article and Find Full Text PDFAbscisic acid-type sesquiterpenes and ansamycins from Amycolatopsis alba DSM 44262.
J Asian Nat Prod Res
October 2017
a Key Laboratory of Chemical Biology (Ministry of Education) , School of Pharmaceutical Sciences, Shandong University, Jinan , China.
Two new abscisic acid-type sesquiterpenes (1, 2), and one new ansamycin (3), together with four known ansamycins, namely ansacarbamitocins 4-7, were isolated from the fermentation extract of Amycolatopsis alba DSM 44262. The structures of the new compounds were elucidated to be (E)-3-methyl-5-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)pent-2-enoic acid (1) and (E)-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-enyl)pent-2-enoic acid (2), and 9-O-methylansacarbamitocin A1 (3), on the basis of comprehensive analysis of spectroscopic data, respectively. The antimicrobial activities were also evaluated for all seven compounds.
View Article and Find Full Text PDFThe ansacarbamitocins: polar ansamitocin derivatives.
J Nat Prod
October 2007
Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, USA.
The ansacarbamitocins are a new family of maytansinoids that are unusually substituted with a glucose subunit and two carbamate functional groups and exhibit modest activity against some agricultural fungal disease organisms. Ansacarbamitocins A-F ( 1- 6) all consist of the same macrocyclic core as the ansamitocins, with variation occurring on the glucose unit, while ansacarbamitocins A1 and B1 ( 7, 8) additionally lack the epoxide group on C-4 and C-5.
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