Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture
Abstract
We prepared the enantiomers of the natural product cycloprodigiosin using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.
- Authors:
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1257348
- Grant/Contract Number:
- AC02-05CH11231; S10-RR027172; 1341894
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Organic Letters
- Additional Journal Information:
- Journal Volume: 17; Journal Issue: 14; Journal ID: ISSN 1523-7060
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., and Sarpong, Richmond. Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture. United States: N. p., 2015.
Web. doi:10.1021/acs.orglett.5b01527.
Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., & Sarpong, Richmond. Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture. United States. https://doi.org/10.1021/acs.orglett.5b01527
Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., and Sarpong, Richmond. Fri .
"Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture". United States. https://doi.org/10.1021/acs.orglett.5b01527. https://www.osti.gov/servlets/purl/1257348.
@article{osti_1257348,
title = {Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture},
author = {Johnson, Rebecca E. and de Rond, Tristan and Lindsay, Vincent N. G. and Keasling, Jay D. and Sarpong, Richmond},
abstractNote = {We prepared the enantiomers of the natural product cycloprodigiosin using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.},
doi = {10.1021/acs.orglett.5b01527},
journal = {Organic Letters},
number = 14,
volume = 17,
place = {United States},
year = {Fri Jul 17 00:00:00 EDT 2015},
month = {Fri Jul 17 00:00:00 EDT 2015}
}
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Cited by: 12 works
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Figures / Tables:
Figure 1.: Representative members in the prodigiosin family of alkaloids.
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Works referenced in this record:
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Application of In Situ-Generated Rh-Bound Trimethylenemethane Variants to the Synthesis of 3,4-Fused Pyrroles
journal, March 2013
- Schultz, Erica E.; Sarpong, Richmond
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C–H Methylation of Heteroarenes Inspired by Radical SAM Methyl Transferase
journal, March 2014
- Gui, Jinghan; Zhou, Qianghui; Pan, Chung-Mao
- Journal of the American Chemical Society, Vol. 136, Issue 13
Elimination of Butylcycloheptylprodigiosin as a Known Natural Product Inspired by an Evolutionary Hypothesis for Cyclic Prodigiosin Biosynthesis
journal, September 2013
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Colour Change of Prodigiosin
journal, October 1968
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- Nature, Vol. 220, Issue 5163
The biosynthesis and regulation of bacterial prodiginines
journal, December 2006
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Prodigiosins uncouple lysosomal vacuolar-type ATPase through promotion of H+/Cl− symport
journal, September 1998
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Works referencing / citing this record:
Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440
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Figures / Tables found in this record:
Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.