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Total Synthesis of Tubiashinol

Sigindere, Cihad (2017) Total Synthesis of Tubiashinol. Master's Thesis, University of Pittsburgh. (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Sigindere, Cihadcis14@pitt.educis14
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairLiu,
Committee MemberDeiters,
Committee MemberIslam,
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

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