Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

Xuan Feng; Nawaf Al Maharik; Axel Bartholome; Jeffrey E. Janso; Usa Reilly; David O'Hagan

doi:10.1039/C7OB02163A

Incorporation of [²H₁]-(1R,2R)- and [²H₁]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

Xuan Feng, Nawaf Al Maharik, Axel Bartholome, Jeffrey E. Janso, Usa Reilly, David O'Hagan

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

Abstract

Deuterium incorporations from [²H₁]-(1R,2R) and [²H₁]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5′ site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5′ of nucleocidin after a feeding experiment with [²H₅]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.

Original language	English
Pages (from-to)	8006-8008
Journal	Organic & Biomolecular Chemistry
Volume	15
Issue number	38
Early online date	11 Sept 2017
DOIs	https://doi.org/10.1039/C7OB02163A
Publication status	Published - 14 Oct 2017

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10.1039/C7OB02163A

O'Hagan_2017_OBC_Streptomycescalvus_AAM
© 2017 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/ 10.1039/C7OB02163A
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title = "Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus",

abstract = "Deuterium incorporations from [2H1]-(1R,2R) and [2H1]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5′ site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5′ of nucleocidin after a feeding experiment with [2H5]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.",

author = "Xuan Feng and {Al Maharik}, Nawaf and Axel Bartholome and Janso, {Jeffrey E.} and Usa Reilly and David O'Hagan",

note = "The authors thank the Chinese Scholarship Council for Ph.D Studentship support (to XF).",

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AU - Al Maharik, Nawaf

AU - Bartholome, Axel

AU - Janso, Jeffrey E.

AU - Reilly, Usa

AU - O'Hagan, David

N1 - The authors thank the Chinese Scholarship Council for Ph.D Studentship support (to XF).

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AB - Deuterium incorporations from [2H1]-(1R,2R) and [2H1]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5′ site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5′ of nucleocidin after a feeding experiment with [2H5]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.

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M3 - Article

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ER -

Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

Abstract

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Incorporation of [²H₁]-(1R,2R)- and [²H₁]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus