Peganutonin A: Computationally Informed Synthesis of Its Revised Structure

N. Sathya Sai Saranya; Rahul Choudhury; Prathmesh R. Supekar; Srinivas Beduru; Craig M. Williams; Mikhail E. Elyashberg; Andrei G. Kutateladze; Roderick W. Bates; D. Srinivasa Reddy

doi:10.1021/acs.jnatprod.5c00322

Peganutonin A: Computationally Informed Synthesis of Its Revised Structure

N. Sathya Sai Saranya, Rahul Choudhury, Prathmesh R. Supekar, Srinivas Beduru, Craig M. Williams, Mikhail E. Elyashberg, Andrei G. Kutateladze, Roderick W. Bates, D. Srinivasa Reddy^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The structure of the recently isolated natural product peganutonin A was shown to be incorrect by analysis of the reported spectroscopic data, and therefore, the structure was reassigned utilizing computational methods. Subsequently, the computationally proposed reassignment was confirmed by total synthesis, which was achieved in seven steps from 6-methoxyindole. It is assumed that peganutonin A is not a natural product but an artifact arising from photooxidation of the alkaloid harmaline.

Original language	English
Journal	Journal of Natural Products
DOIs	https://doi.org/10.1021/acs.jnatprod.5c00322
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society and American Society of Pharmacognosy.

ASJC Scopus Subject Areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Peganutonin A: Computationally Informed Synthesis of Its Revised Structure",

abstract = "The structure of the recently isolated natural product peganutonin A was shown to be incorrect by analysis of the reported spectroscopic data, and therefore, the structure was reassigned utilizing computational methods. Subsequently, the computationally proposed reassignment was confirmed by total synthesis, which was achieved in seven steps from 6-methoxyindole. It is assumed that peganutonin A is not a natural product but an artifact arising from photooxidation of the alkaloid harmaline.",

author = "Saranya, {N. Sathya Sai} and Rahul Choudhury and Supekar, {Prathmesh R.} and Srinivas Beduru and Williams, {Craig M.} and Elyashberg, {Mikhail E.} and Kutateladze, {Andrei G.} and Bates, {Roderick W.} and Reddy, {D. Srinivasa}",

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year = "2025",

doi = "10.1021/acs.jnatprod.5c00322",

language = "English",

journal = "Journal of Natural Products",

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T2 - Computationally Informed Synthesis of Its Revised Structure

AU - Saranya, N. Sathya Sai

AU - Choudhury, Rahul

AU - Supekar, Prathmesh R.

AU - Beduru, Srinivas

AU - Williams, Craig M.

AU - Elyashberg, Mikhail E.

AU - Kutateladze, Andrei G.

AU - Bates, Roderick W.

AU - Reddy, D. Srinivasa

PY - 2025

Y1 - 2025

N2 - The structure of the recently isolated natural product peganutonin A was shown to be incorrect by analysis of the reported spectroscopic data, and therefore, the structure was reassigned utilizing computational methods. Subsequently, the computationally proposed reassignment was confirmed by total synthesis, which was achieved in seven steps from 6-methoxyindole. It is assumed that peganutonin A is not a natural product but an artifact arising from photooxidation of the alkaloid harmaline.

AB - The structure of the recently isolated natural product peganutonin A was shown to be incorrect by analysis of the reported spectroscopic data, and therefore, the structure was reassigned utilizing computational methods. Subsequently, the computationally proposed reassignment was confirmed by total synthesis, which was achieved in seven steps from 6-methoxyindole. It is assumed that peganutonin A is not a natural product but an artifact arising from photooxidation of the alkaloid harmaline.

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SN - 0163-3864

JO - Journal of Natural Products

JF - Journal of Natural Products

ER -

Peganutonin A: Computationally Informed Synthesis of Its Revised Structure

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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