Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus

Axel Bartholomé; Jeffrey E. Janso; Usa Reilly; David O'Hagan

doi:10.1039/C6OB02291J

Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus

Axel Bartholomé, Jeffrey E. Janso, Usa Reilly, David O'Hagan

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

Abstract

Deuterium and carbon-13 labelled glycerols have been fed to Streptomyces calvus fermentations and isotope incorporation into the fluorine containing antibiotic nucleocidin have been evaluated by ¹⁹F-NMR. A single deuterium atom was incorporated from [²H₅]- and (R)-[²H₂]- glycerol into C-5’ of the antibiotic, suggesting that an oxidation occurs at this carbon after ribose ring assembly from glycerol (pentose phosphate pathway), during nucleocidin biosynthesis.

Original language	English
Pages (from-to)	61-64
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	15
Issue number	1
Early online date	9 Nov 2016
DOIs	https://doi.org/10.1039/C6OB02291J
Publication status	Published - 7 Jan 2017

Access to Document

10.1039/C6OB02291J

Main Text_AxelOBC7thNov
© 2016 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 may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1039/C6OB02291J
Accepted author manuscript, 575 KB
Sup Info_Supplementary OBC 7hNovAccepted author manuscript, 2.11 MB

Cite this

@article{064ce60616dd4143be8110a5ebad39fe,

title = "Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus",

abstract = "Deuterium and carbon-13 labelled glycerols have been fed to Streptomyces calvus fermentations and isotope incorporation into the fluorine containing antibiotic nucleocidin have been evaluated by 19F-NMR. A single deuterium atom was incorporated from [2H5]- and (R)-[2H2]- glycerol into C-5{\textquoteright} of the antibiotic, suggesting that an oxidation occurs at this carbon after ribose ring assembly from glycerol (pentose phosphate pathway), during nucleocidin biosynthesis. ",

author = "Axel Bartholom{\'e} and Janso, {Jeffrey E.} and Usa Reilly and David O'Hagan",

year = "2017",

month = jan,

day = "7",

doi = "10.1039/C6OB02291J",

language = "English",

volume = "15",

pages = "61--64",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Fluorometabolite biosynthesis

T2 - isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus

AU - Bartholomé, Axel

AU - Janso, Jeffrey E.

AU - Reilly, Usa

AU - O'Hagan, David

PY - 2017/1/7

Y1 - 2017/1/7

N2 - Deuterium and carbon-13 labelled glycerols have been fed to Streptomyces calvus fermentations and isotope incorporation into the fluorine containing antibiotic nucleocidin have been evaluated by 19F-NMR. A single deuterium atom was incorporated from [2H5]- and (R)-[2H2]- glycerol into C-5’ of the antibiotic, suggesting that an oxidation occurs at this carbon after ribose ring assembly from glycerol (pentose phosphate pathway), during nucleocidin biosynthesis.

AB - Deuterium and carbon-13 labelled glycerols have been fed to Streptomyces calvus fermentations and isotope incorporation into the fluorine containing antibiotic nucleocidin have been evaluated by 19F-NMR. A single deuterium atom was incorporated from [2H5]- and (R)-[2H2]- glycerol into C-5’ of the antibiotic, suggesting that an oxidation occurs at this carbon after ribose ring assembly from glycerol (pentose phosphate pathway), during nucleocidin biosynthesis.

U2 - 10.1039/C6OB02291J

DO - 10.1039/C6OB02291J

M3 - Article

SN - 1477-0520

VL - 15

SP - 61

EP - 64

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 1

ER -

Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus

Abstract

Access to Document

Fingerprint

Cite this