Halogenated adenine and adenosine natural products in Streptomyces sp. JCM9888

Yawen Chen; Phillip Lowe; Hai Deng; David O'Hagan

doi:10.1002/ejoc.202400578

Halogenated adenine and adenosine natural products in Streptomyces sp. JCM9888

Yawen Chen, Phillip Lowe, Hai Deng, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

Ascamycin 1 and dealanylascamycin 2 are adenosine containing nucleoside antibiotics carrying the rare 5’-O-sulfamoyl ribose motif and a chlorine atom attached to C2 of the adenine ring. Gene knockouts (ΔacmK and ΔacmJ) in the producing strain, Streptomyces sp. JCM9888, generated mutants that were disabled in the assembly of the sulfamoyl moiety. This resulted in the production of 2-chloroadenosine 3 and 2-chloroadenine 4, indicating that purine halogenation can occur independently of sulfamoylation. Incubations in media enriched in bromide content resulted also in the identification of 2-bromoadenine 5, 2-bromoadenosine 6 and 5′-O-sulfamoyl-2-bromoadenosine 7.

Original language	English
Article number	e202400578
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	Early View
Early online date	30 Oct 2024
DOIs	https://doi.org/10.1002/ejoc.202400578
Publication status	E-pub ahead of print - 30 Oct 2024

Keywords

Ascamycin
Natural products
Nucleosides
Streptomyces

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Copyright © 2024 The Authors. This is an open access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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Cite this

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title = "Halogenated adenine and adenosine natural products in Streptomyces sp. JCM9888",

abstract = "Ascamycin 1 and dealanylascamycin 2 are adenosine containing nucleoside antibiotics carrying the rare 5{\textquoteright}-O-sulfamoyl ribose motif and a chlorine atom attached to C2 of the adenine ring. Gene knockouts (ΔacmK and ΔacmJ) in the producing strain, Streptomyces sp. JCM9888, generated mutants that were disabled in the assembly of the sulfamoyl moiety. This resulted in the production of 2-chloroadenosine 3 and 2-chloroadenine 4, indicating that purine halogenation can occur independently of sulfamoylation. Incubations in media enriched in bromide content resulted also in the identification of 2-bromoadenine 5, 2-bromoadenosine 6 and 5′-O-sulfamoyl-2-bromoadenosine 7.",

keywords = "Ascamycin, Natural products, Nucleosides, Streptomyces",

author = "Yawen Chen and Phillip Lowe and Hai Deng and David O'Hagan",

note = "Funding: The authors thank the EPSRC and the Leverhulme Trusts for financial support. The Chinese Scholarship Council is also acknowledged for studentship support (Y.C.).",

year = "2024",

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doi = "10.1002/ejoc.202400578",

language = "English",

volume = "Early View",

journal = "European Journal of Organic Chemistry",

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T1 - Halogenated adenine and adenosine natural products in Streptomyces sp. JCM9888

AU - Chen, Yawen

AU - Lowe, Phillip

AU - Deng, Hai

AU - O'Hagan, David

N1 - Funding: The authors thank the EPSRC and the Leverhulme Trusts for financial support. The Chinese Scholarship Council is also acknowledged for studentship support (Y.C.).

PY - 2024/10/30

Y1 - 2024/10/30

N2 - Ascamycin 1 and dealanylascamycin 2 are adenosine containing nucleoside antibiotics carrying the rare 5’-O-sulfamoyl ribose motif and a chlorine atom attached to C2 of the adenine ring. Gene knockouts (ΔacmK and ΔacmJ) in the producing strain, Streptomyces sp. JCM9888, generated mutants that were disabled in the assembly of the sulfamoyl moiety. This resulted in the production of 2-chloroadenosine 3 and 2-chloroadenine 4, indicating that purine halogenation can occur independently of sulfamoylation. Incubations in media enriched in bromide content resulted also in the identification of 2-bromoadenine 5, 2-bromoadenosine 6 and 5′-O-sulfamoyl-2-bromoadenosine 7.

AB - Ascamycin 1 and dealanylascamycin 2 are adenosine containing nucleoside antibiotics carrying the rare 5’-O-sulfamoyl ribose motif and a chlorine atom attached to C2 of the adenine ring. Gene knockouts (ΔacmK and ΔacmJ) in the producing strain, Streptomyces sp. JCM9888, generated mutants that were disabled in the assembly of the sulfamoyl moiety. This resulted in the production of 2-chloroadenosine 3 and 2-chloroadenine 4, indicating that purine halogenation can occur independently of sulfamoylation. Incubations in media enriched in bromide content resulted also in the identification of 2-bromoadenine 5, 2-bromoadenosine 6 and 5′-O-sulfamoyl-2-bromoadenosine 7.

KW - Ascamycin

KW - Natural products

KW - Nucleosides

KW - Streptomyces

U2 - 10.1002/ejoc.202400578

DO - 10.1002/ejoc.202400578

M3 - Article

SN - 1434-193X

VL - Early View

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

M1 - e202400578

ER -

Halogenated adenine and adenosine natural products in Streptomyces sp. JCM9888

Abstract

Keywords

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