Published February 15, 2019
| Version Supplemental Material + Accepted Version
Journal Article
Open
Semisynthesis of an Anticancer DPAGT1 Inhibitor from a Muraymycin Biosynthetic Intermediate
Creators
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1.
University of Tennessee Health Science Center
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2.
California Institute of Technology
Abstract
We have explored a method to convert a muraymycin biosynthetic intermediate 3 to an anticancer drug lead 2 for in vivo and thorough preclinical studies. Cu(OAc)₂ forms a stable complex with the amide 4 and prevents electrophilic reactions at the 2-((3-aminopropyl)amino)acetamide moiety. Under the present conditions, the desired 5″-primary amine was selectively protected with (Boc)₂O to yield 6. The intermediate 6 was converted to 2 in two steps with 90% yield.
Additional Information
© 2019 American Chemical Society. Received: November 20, 2018; Published: January 30, 2019. We thank the National Institutes of Health (Grant No. GM114611). M.K. also thanks the University of Tennessee Health Science Center for generous financial support (UTHSC College of Pharmacy, CORNET, and UTRF awards). NMR data were obtained on instruments supported by the NIH Shared Instrumentation Grant. Streptomyces sp. NRRL 30471 was acquired from USDA (NRRL Culture Collection). The authors declare no competing financial interest.Attached Files
Accepted Version - nihms-1008789.pdf
Supplemental Material - ol8b03716_si_001.pdf
Files
nihms-1008789.pdf
Additional details
Additional titles
- Alternative title
- A Semi-Synthesis of an Anticancer DPAGT1 Inhibitor from a Muraymycin Biosynthetic Intermediate
Identifiers
- PMCID
- PMC6447083
- Eprint ID
- 92532
- Resolver ID
- CaltechAUTHORS:20190130-162009556
Funding
- NIH
- GM114611
- University of Tennessee
Dates
- Created
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2019-01-31Created from EPrint's datestamp field
- Updated
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2022-03-01Created from EPrint's last_modified field