Sigindere, Cihad
(2017)
Total Synthesis of Tubiashinol.
Master's Thesis, University of Pittsburgh.
(Unpublished)
This is the latest version of this item.
Abstract
The genus Vibrio harbors over 100 species and some of them are well-known (e.g. Vibrio anguillarum and Vibrio cholerae.) They are Gram-negative and comma-shaped bacteria which are present within many diverse marine organisms and habitats, such as mollusks, shrimps, fishes, and corals. They have an array of extracellular products some of which cause toxicity.
Another species, Vibrio tubiashii, is found in Pacific Ocean and has shown to be a prevalent pathogen of oyster larvae. It increasingly affects oyster populations as well as being a problem for oyster hatcheries, nurseries and farms. With implementing genome mining, our group has identified a gene cluster which is responsible for a bio-pathway of couple metabolites. Isolated and characterized authentic samples were used in a collaborative study and one of the metabolites showed toxicity towards oyster larvae and zebra fish embryo. After this observation, we become interested in the synthesis of this toxic marine natural product and named it tubiashinol.
The coupling of the first 2 building blocks was achieved after testing few different agents and the diastereomerically pure dipeptide (N-terminus) was obtained. However, synthesis of (3R,4S)-4-amino-6-methylheptane-1,3-diol (C-terminal) was challenging and we had to try number of strategies to attain the desired amino-diol. In the process, we also obtained the 3-epi diastereomer and the absolute stereochemistry of its precursor was determined by X-Ray which fortified our characterizations. This diastereomer was, then, used to synthesize 3-epi tubiashinol which was compared to tubiashinol later.
In this study, we reported the first Vibrio tubiashii metabolite which is toxic to oyster larvae. We successfully synthesized and characterized tubiashinol and 3-epi tubiashinol and compared them to determine the absolute stereochemistry of tubiashinol in proton (1H) NMR studies.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
21 September 2017 |
| Date Type: |
Publication |
| Defense Date: |
23 May 2017 |
| Approval Date: |
21 September 2017 |
| Submission Date: |
23 July 2017 |
| Access Restriction: |
5 year -- Restrict access to University of Pittsburgh for a period of 5 years. |
| Number of Pages: |
89 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Vibrio tubiashii, V. tubiashii, vibrio, tubiashii, tubiashinol, total synthesis, probe design |
| Date Deposited: |
21 Sep 2017 23:46 |
| Last Modified: |
21 Sep 2022 05:15 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/32913 |
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Total Synthesis of Tubiashinol. (deposited 21 Sep 2017 23:46)
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