3'-O-β-Glucosyl-4',5'-didehydro-5'-deoxyadenosine Is a Natural Product of the Nucleocidin Producers Streptomyces virens and Streptomyces calvus.

Xuan Feng; Qingzhi Zhang; David J Clarke; Hai Deng; 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.

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

Chemistry

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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- 2H 2]-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

Bibliographical note

We thank the Leverhulme Trust (RPG-2021-028) for financial support. We also thank Pfizer Ltd. (Groton, USA) for supplying the nucleocidin-producing strain S. calvus T-3018.

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Copyright © 2023 The Authors. Published by American Chemical Society and American Society of Pharmacognosy. This publication is licensed under CC-BY 4.0. https://creativecommons.org/licenses/by/4.0/
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@article{6c5bfb15288149c592aca0ef3d94259e,

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- 2H 2]-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 = "Xuan Feng and Qingzhi Zhang and Clarke, {David J} and Hai Deng and David O'Hagan",

note = "We thank the Leverhulme Trust (RPG-2021-028) for financial support. We also thank Pfizer Ltd. (Groton, USA) for supplying the nucleocidin-producing strain S. calvus T-3018.",

year = "2023",

month = oct,

day = "27",

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

language = "English",

volume = "86",

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journal = "Journal of Natural Products",

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TY - JOUR

T1 - 3'-O-β-Glucosyl-4',5'-didehydro-5'-deoxyadenosine Is a Natural Product of the Nucleocidin Producers Streptomyces virens and Streptomyces calvus.

AU - Feng, Xuan

AU - Zhang, Qingzhi

AU - Clarke, David J

AU - Deng, Hai

AU - O'Hagan, David

N1 - We thank the Leverhulme Trust (RPG-2021-028) for financial support. We also thank Pfizer Ltd. (Groton, USA) for supplying the nucleocidin-producing strain S. calvus T-3018.

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- 2H 2]-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- 2H 2]-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

C2 - 37748016

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.

Abstract

Bibliographical note

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