Total Synthesis of Desmethyl Jahanyne and Its Lipo-Tetrapeptide Conjugates Derived from Parent Skeleton as BCL-2-Mediated Apoptosis-Inducing Agents | Zendy

Shivakrishna Kallepu | Zendy; M. Kavitha | Zendy; Ragini Yeeravalli | Zendy; Kanakaraju Manupati | Zendy; Surender Singh Jadav | Zendy; Amitava Das | Zendy; Prathama S. Mainkar | Zendy; S. Chandrasekhar | Zendy

Open Access

Total Synthesis of Desmethyl Jahanyne and Its Lipo-Tetrapeptide Conjugates Derived from Parent Skeleton as BCL-2-Mediated Apoptosis-Inducing Agents

Author(s) -

Shivakrishna Kallepu,

M. Kavitha,

Ragini Yeeravalli,

Kanakaraju Manupati,

Surender Singh Jadav,

Amitava Das,

Prathama S. Mainkar,

S. Chandrasekhar

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01634

Subject(s) - tetrapeptide , natural product , total synthesis , desmethyl , apoptosis , stereochemistry , chemistry , conjugate , combinatorial chemistry , biochemistry , metabolite , peptide , mathematical analysis , mathematics

The total synthesis of highly potent and scarcely available marine natural product (-)-jahanyne was attempted resulting in a solution-phase synthesis of pruned versions with comparable activity. A simple and facile synthetic route was employed for the preparation of pruned congeners and would be scalable. The lipophilic tail of the natural product was synthesized from R -(+)-citronellol, utilizing easily available chemicals. All the synthesized compounds were screened for apoptotic activity against a panel of cell lines. These compounds depicted marked binding to B cell lymphoma 2 till 50 °C in cellular thermal shift analysis.

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