What question did this study set out to answer?

To resolve the unknown chemical identity and solution conformation of rapamycin's minor isomer.

July 11, 2023Journal of Natural ProductsOpen Access

Unmasking the True Identity of Rapamycin’s Minor Conformer

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Authors

ECEmily B. CrullUniversity of North Carolina Wilmington AJAjay N. JainOptibrium (United Kingdom)PHPaul C. D. HawkinsAndrews University

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Implication

Structural investigation reveals rapamycin's minor solution conformer is a trans amide with ester rotation, highlighting a decades-long misassignment based on FK-506.

Key Points

To resolve the unknown chemical identity and solution conformation of rapamycin's minor isomer.
Analyzed the solution conformation of rapamycin using nuclear magnetic resonance (NMR) spectroscopy techniques.
Modeled candidate conformational isomers using computational methods to evaluate relative stability and geometry.
Identified rapamycin's minor solution conformer as a trans amide species characterized by rotation about the ester linkage.
Refuted the prevailing five-decade-old assumption that the minor conformer exists as a cis amide analogous to FK-506.

Cite This Study

Crull et al. (2023) studied this question.

synapsesocial.com/papers/6a9ec3aa110f11dd1ebe3366 https://doi.org/10.1021/acs.jnatprod.3c00421

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Implication

Structural investigation reveals rapamycin's minor solution conformer is a trans amide with ester rotation, highlighting a decades-long misassignment based on FK-506.

Unmasking the True Identity of Rapamycin’s Minor Conformer

Discussion

Member takes

Implication

Key Points

Cite This Study

Unmasking the True Identity of Rapamycin’s Minor Conformer

Discussion

Member takes

Implication

Key Points

Cite This Study

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