3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine is a natural product of the nucleocidin producers Streptomyces virens and Streptomyces calvus

David Clarke; Xuan Feng; Hai Deng; Qingzhi Zhang; David O'Hagan

doi:10.1021/acs.jnatprod.3c00521

3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine is a natural product of the nucleocidin producers Streptomyces virens and Streptomyces calvus

David Clarke, Xuan Feng, Hai Deng, Qingzhi Zhang, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 is identified as a natural product of Streptomyces calvus and Streptomyces virens. It is also generated in vitro by direct β-glucosylation of 4′,5′-didehydro-5′-deoxyadenosine 12 with the enzyme NucGT. The intact incorporation of oxygen-18 and deuterium isotopes from (±)[1-18O,1-2H2]-glycerol 14 into C-5′ of nucleocidin 1 and its related metabolites precludes 3′-O-β-glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 as a biosynthetic precursor to nucleocidin 1.

Original language	English
Pages (from-to)	2326-2332
Number of pages	7
Journal	Journal of Natural Products
Volume	86
Issue number	10
Early online date	25 Sept 2023
DOIs	https://doi.org/10.1021/acs.jnatprod.3c00521
Publication status	Published - 27 Oct 2023

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10.1021/acs.jnatprod.3c00521Licence: CC BY

Feng_2023_JNP_3OB-glucosyl_CC
Copyright © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.
Final published version, 2.41 MBLicence: CC BY

Identification of a Flourination Enzyme: Identification of a fluorination enzyme involved in nucleocidin biosynthesis
O'Hagan, D. (PI)
The Leverhulme Trust
1/05/21 → 30/04/24
Project: Standard

3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine Is a Natural Product of the Nucleocidin Producers Streptomyces virens and Streptomyces calvus (code)
Feng, X. (Creator), University of St Andrews, 5 Sept 2024
DOI: 10.17630/db73578e-2889-4ee4-a897-e257da2a8b5b
Dataset: Software

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title = "3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine is a natural product of the nucleocidin producers Streptomyces virens and Streptomyces calvus",

abstract = "3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 is identified as a natural product of Streptomyces calvus and Streptomyces virens. It is also generated in vitro by direct β-glucosylation of 4′,5′-didehydro-5′-deoxyadenosine 12 with the enzyme NucGT. The intact incorporation of oxygen-18 and deuterium isotopes from (±)[1-18O,1-2H2]-glycerol 14 into C-5′ of nucleocidin 1 and its related metabolites precludes 3′-O-β-glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 as a biosynthetic precursor to nucleocidin 1.",

author = "David Clarke and Xuan Feng and Hai Deng and Qingzhi Zhang and David O'Hagan",

note = "Funding: Leverhulme Trust - RPG-2021-028.",

year = "2023",

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doi = "10.1021/acs.jnatprod.3c00521",

language = "English",

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T1 - 3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine is a natural product of the nucleocidin producers Streptomyces virens and Streptomyces calvus

AU - Clarke, David

AU - Feng, Xuan

AU - Deng, Hai

AU - Zhang, Qingzhi

AU - O'Hagan, David

N1 - Funding: Leverhulme Trust - RPG-2021-028.

PY - 2023/10/27

Y1 - 2023/10/27

N2 - 3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 is identified as a natural product of Streptomyces calvus and Streptomyces virens. It is also generated in vitro by direct β-glucosylation of 4′,5′-didehydro-5′-deoxyadenosine 12 with the enzyme NucGT. The intact incorporation of oxygen-18 and deuterium isotopes from (±)[1-18O,1-2H2]-glycerol 14 into C-5′ of nucleocidin 1 and its related metabolites precludes 3′-O-β-glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 as a biosynthetic precursor to nucleocidin 1.

AB - 3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 is identified as a natural product of Streptomyces calvus and Streptomyces virens. It is also generated in vitro by direct β-glucosylation of 4′,5′-didehydro-5′-deoxyadenosine 12 with the enzyme NucGT. The intact incorporation of oxygen-18 and deuterium isotopes from (±)[1-18O,1-2H2]-glycerol 14 into C-5′ of nucleocidin 1 and its related metabolites precludes 3′-O-β-glucosyl-4′,5′-didehydro-5′-deoxyadenosine 13 as a biosynthetic precursor to nucleocidin 1.

U2 - 10.1021/acs.jnatprod.3c00521

DO - 10.1021/acs.jnatprod.3c00521

M3 - Article

SN - 0163-3864

VL - 86

SP - 2326

EP - 2332

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 10

ER -

3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine is a natural product of the nucleocidin producers Streptomyces virens and Streptomyces calvus

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Identification of a Flourination Enzyme: Identification of a fluorination enzyme involved in nucleocidin biosynthesis

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3′-O-β-Glucosyl-4′,5′-didehydro-5′-deoxyadenosine Is a Natural Product of the Nucleocidin Producers Streptomyces virens and Streptomyces calvus (code)

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