Four additional natural 7-deazaguanine derivatives in phages and how to make them

Research output: Contribution to journal › Journal article › Research › peer-review

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Four additional natural 7-deazaguanine derivatives in phages and how to make them. / Cui, Liang; Balamkundu, Seetharamsing; Liu, Chuan Fa; Ye, Hong; Hourihan, Jacob; Rausch, Astrid; Hauß, Christopher; Nilsson, Emelie; Hoetzinger, Matthias; Holmfeldt, Karin; Zhang, Weijia; Martinez-Alvarez, Laura; Peng, Xu; Tremblay, Denise; Moinau, Sylvain; Solonenko, Natalie; Sullivan, Matthew B.; Lee, Yan Jiun; Mulholland, Andrew; Weigele, Peter R.; de Crécy-Lagard, Valérie; Dedon, Peter C.; Hutinet, Geoffrey.

In: Nucleic Acids Research, Vol. 51, No. 17, 2023, p. 9214-9226.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Cui, L, Balamkundu, S, Liu, CF, Ye, H, Hourihan, J, Rausch, A, Hauß, C, Nilsson, E, Hoetzinger, M, Holmfeldt, K, Zhang, W, Martinez-Alvarez, L, Peng, X, Tremblay, D, Moinau, S, Solonenko, N, Sullivan, MB, Lee, YJ, Mulholland, A, Weigele, PR, de Crécy-Lagard, V, Dedon, PC & Hutinet, G 2023, 'Four additional natural 7-deazaguanine derivatives in phages and how to make them', Nucleic Acids Research, vol. 51, no. 17, pp. 9214-9226. https://doi.org/10.1093/nar/gkad657

APA

Cui, L., Balamkundu, S., Liu, C. F., Ye, H., Hourihan, J., Rausch, A., Hauß, C., Nilsson, E., Hoetzinger, M., Holmfeldt, K., Zhang, W., Martinez-Alvarez, L., Peng, X., Tremblay, D., Moinau, S., Solonenko, N., Sullivan, M. B., Lee, Y. J., Mulholland, A., ... Hutinet, G. (2023). Four additional natural 7-deazaguanine derivatives in phages and how to make them. Nucleic Acids Research, 51(17), 9214-9226. https://doi.org/10.1093/nar/gkad657

Vancouver

Cui L, Balamkundu S, Liu CF, Ye H, Hourihan J, Rausch A et al. Four additional natural 7-deazaguanine derivatives in phages and how to make them. Nucleic Acids Research. 2023;51(17):9214-9226. https://doi.org/10.1093/nar/gkad657

Author

Cui, Liang ; Balamkundu, Seetharamsing ; Liu, Chuan Fa ; Ye, Hong ; Hourihan, Jacob ; Rausch, Astrid ; Hauß, Christopher ; Nilsson, Emelie ; Hoetzinger, Matthias ; Holmfeldt, Karin ; Zhang, Weijia ; Martinez-Alvarez, Laura ; Peng, Xu ; Tremblay, Denise ; Moinau, Sylvain ; Solonenko, Natalie ; Sullivan, Matthew B. ; Lee, Yan Jiun ; Mulholland, Andrew ; Weigele, Peter R. ; de Crécy-Lagard, Valérie ; Dedon, Peter C. ; Hutinet, Geoffrey. / Four additional natural 7-deazaguanine derivatives in phages and how to make them. In: Nucleic Acids Research. 2023 ; Vol. 51, No. 17. pp. 9214-9226.

Bibtex

@article{cda18b5d3d2c4ef2af4a037b7a7ff2bb,
title = "Four additional natural 7-deazaguanine derivatives in phages and how to make them",
abstract = "Bacteriophages and bacteria are engaged in a constant arms race, continually evolving new molecular tools to survive one another. To protect their genomic DNA from restriction enzymes, the most common bacterial defence systems, double-stranded DNA phages have evolved complex modifications that affect all four bases. This study focuses on modifications at position 7 of guanines. Eight derivatives of 7-deazaguanines were identified, including four previously unknown ones: 2'-deoxy-7-(methylamino)methyl-7-deazaguanine (mdPreQ1), 2'-deoxy-7-(formylamino)methyl-7-deazaguanine (fdPreQ1), 2'-deoxy-7-deazaguanine (dDG) and 2'-deoxy-7-carboxy-7-deazaguanine (dCDG). These modifications are inserted in DNA by a guanine transglycosylase named DpdA. Three subfamilies of DpdA had been previously characterized: bDpdA, DpdA1, and DpdA2. Two additional subfamilies were identified in this work: DpdA3, which allows for complete replacement of the guanines, and DpdA4, which is specific to archaeal viruses. Transglycosylases have now been identified in all phages and viruses carrying 7-deazaguanine modifications, indicating that the insertion of these modifications is a post-replication event. Three enzymes were predicted to be involved in the biosynthesis of these newly identified DNA modifications: 7-carboxy-7-deazaguanine decarboxylase (DpdL), dPreQ1 formyltransferase (DpdN) and dPreQ1 methyltransferase (DpdM), which was experimentally validated and harbors a unique fold not previously observed for nucleic acid methylases.",
author = "Liang Cui and Seetharamsing Balamkundu and Liu, {Chuan Fa} and Hong Ye and Jacob Hourihan and Astrid Rausch and Christopher Hau{\ss} and Emelie Nilsson and Matthias Hoetzinger and Karin Holmfeldt and Weijia Zhang and Laura Martinez-Alvarez and Xu Peng and Denise Tremblay and Sylvain Moinau and Natalie Solonenko and Sullivan, {Matthew B.} and Lee, {Yan Jiun} and Andrew Mulholland and Weigele, {Peter R.} and {de Cr{\'e}cy-Lagard}, Val{\'e}rie and Dedon, {Peter C.} and Geoffrey Hutinet",
note = "Publisher Copyright: {\textcopyright} The Author(s) 2023. Published by Oxford University Press on behalf of Nucleic Acids Research.",
year = "2023",
doi = "10.1093/nar/gkad657",
language = "English",
volume = "51",
pages = "9214--9226",
journal = "Nucleic Acids Research",
issn = "0305-1048",
publisher = "Oxford University Press",
number = "17",

}

RIS

TY - JOUR

T1 - Four additional natural 7-deazaguanine derivatives in phages and how to make them

AU - Cui, Liang

AU - Balamkundu, Seetharamsing

AU - Liu, Chuan Fa

AU - Ye, Hong

AU - Hourihan, Jacob

AU - Rausch, Astrid

AU - Hauß, Christopher

AU - Nilsson, Emelie

AU - Hoetzinger, Matthias

AU - Holmfeldt, Karin

AU - Zhang, Weijia

AU - Martinez-Alvarez, Laura

AU - Peng, Xu

AU - Tremblay, Denise

AU - Moinau, Sylvain

AU - Solonenko, Natalie

AU - Sullivan, Matthew B.

AU - Lee, Yan Jiun

AU - Mulholland, Andrew

AU - Weigele, Peter R.

AU - de Crécy-Lagard, Valérie

AU - Dedon, Peter C.

AU - Hutinet, Geoffrey

N1 - Publisher Copyright: © The Author(s) 2023. Published by Oxford University Press on behalf of Nucleic Acids Research.

PY - 2023

Y1 - 2023

N2 - Bacteriophages and bacteria are engaged in a constant arms race, continually evolving new molecular tools to survive one another. To protect their genomic DNA from restriction enzymes, the most common bacterial defence systems, double-stranded DNA phages have evolved complex modifications that affect all four bases. This study focuses on modifications at position 7 of guanines. Eight derivatives of 7-deazaguanines were identified, including four previously unknown ones: 2'-deoxy-7-(methylamino)methyl-7-deazaguanine (mdPreQ1), 2'-deoxy-7-(formylamino)methyl-7-deazaguanine (fdPreQ1), 2'-deoxy-7-deazaguanine (dDG) and 2'-deoxy-7-carboxy-7-deazaguanine (dCDG). These modifications are inserted in DNA by a guanine transglycosylase named DpdA. Three subfamilies of DpdA had been previously characterized: bDpdA, DpdA1, and DpdA2. Two additional subfamilies were identified in this work: DpdA3, which allows for complete replacement of the guanines, and DpdA4, which is specific to archaeal viruses. Transglycosylases have now been identified in all phages and viruses carrying 7-deazaguanine modifications, indicating that the insertion of these modifications is a post-replication event. Three enzymes were predicted to be involved in the biosynthesis of these newly identified DNA modifications: 7-carboxy-7-deazaguanine decarboxylase (DpdL), dPreQ1 formyltransferase (DpdN) and dPreQ1 methyltransferase (DpdM), which was experimentally validated and harbors a unique fold not previously observed for nucleic acid methylases.

AB - Bacteriophages and bacteria are engaged in a constant arms race, continually evolving new molecular tools to survive one another. To protect their genomic DNA from restriction enzymes, the most common bacterial defence systems, double-stranded DNA phages have evolved complex modifications that affect all four bases. This study focuses on modifications at position 7 of guanines. Eight derivatives of 7-deazaguanines were identified, including four previously unknown ones: 2'-deoxy-7-(methylamino)methyl-7-deazaguanine (mdPreQ1), 2'-deoxy-7-(formylamino)methyl-7-deazaguanine (fdPreQ1), 2'-deoxy-7-deazaguanine (dDG) and 2'-deoxy-7-carboxy-7-deazaguanine (dCDG). These modifications are inserted in DNA by a guanine transglycosylase named DpdA. Three subfamilies of DpdA had been previously characterized: bDpdA, DpdA1, and DpdA2. Two additional subfamilies were identified in this work: DpdA3, which allows for complete replacement of the guanines, and DpdA4, which is specific to archaeal viruses. Transglycosylases have now been identified in all phages and viruses carrying 7-deazaguanine modifications, indicating that the insertion of these modifications is a post-replication event. Three enzymes were predicted to be involved in the biosynthesis of these newly identified DNA modifications: 7-carboxy-7-deazaguanine decarboxylase (DpdL), dPreQ1 formyltransferase (DpdN) and dPreQ1 methyltransferase (DpdM), which was experimentally validated and harbors a unique fold not previously observed for nucleic acid methylases.

U2 - 10.1093/nar/gkad657

DO - 10.1093/nar/gkad657

M3 - Journal article

C2 - 37572349

AN - SCOPUS:85172424676

VL - 51

SP - 9214

EP - 9226

JO - Nucleic Acids Research

JF - Nucleic Acids Research

SN - 0305-1048

IS - 17

ER -

ID: 369347749