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- Name help_outline (2S)-2-amino-2'-deoxyadenylo-succinate Identifier CHEBI:172924 Charge -4 Formula C14H15N6O10P InChIKeyhelp_outline GOIAPHWMMMFKRU-RULNZFCNSA-J SMILEShelp_outline N1(C2=C(C(N[C@@H](CC([O-])=O)C([O-])=O)=NC(=N2)N)N=C1)[C@@H]3O[C@H](COP([O-])([O-])=O)[C@H](C3)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dZMP Identifier CHEBI:172927 Charge -2 Formula C10H13N6O6P InChIKeyhelp_outline RZZBUMCFKOLHEH-KVQBGUIXSA-L SMILEShelp_outline N1(C2=C(C(N)=NC(=N2)N)N=C1)[C@@H]3O[C@H](COP([O-])([O-])=O)[C@H](C3)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline fumarate Identifier CHEBI:29806 (CAS: 142-42-7) help_outline Charge -2 Formula C4H2O4 InChIKeyhelp_outline VZCYOOQTPOCHFL-OWOJBTEDSA-L SMILEShelp_outline [O-]C(=O)\C=C\C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 41 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:67636 | RHEA:67637 | RHEA:67638 | RHEA:67639 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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A third purine biosynthetic pathway encoded by aminoadenine-based viral DNA genomes.
Sleiman D., Garcia P.S., Lagune M., Loc'h J., Haouz A., Taib N., Roethlisberger P., Gribaldo S., Marliere P., Kaminski P.A.
Cells have two purine pathways that synthesize adenine and guanine ribonucleotides from phosphoribose via inosylate. A chemical hybrid between adenine and guanine, 2-aminoadenine (Z), replaces adenine in the DNA of the cyanobacterial virus S-2L. We show that S-2L and <i>Vibrio</i> phage PhiVC8 enc ... >> More
Cells have two purine pathways that synthesize adenine and guanine ribonucleotides from phosphoribose via inosylate. A chemical hybrid between adenine and guanine, 2-aminoadenine (Z), replaces adenine in the DNA of the cyanobacterial virus S-2L. We show that S-2L and <i>Vibrio</i> phage PhiVC8 encode a third purine pathway catalyzed by PurZ, a distant paralog of succinoadenylate synthase (PurA), the enzyme condensing aspartate and inosylate in the adenine pathway. PurZ condenses aspartate with deoxyguanylate into dSMP (N6-succino-2-amino-2'-deoxyadenylate), which undergoes defumarylation and phosphorylation to give dZTP (2-amino-2'-deoxyadenosine-5'-triphosphate), a substrate for the phage DNA polymerase. Crystallography and phylogenetics analyses indicate a close relationship between phage PurZ and archaeal PurA enzymes. Our work elucidates the biocatalytic innovation that remodeled a DNA building block beyond canonical molecular biology. << Less
Science 372:516-520(2021) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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A widespread pathway for substitution of adenine by diaminopurine in phage genomes.
Zhou Y., Xu X., Wei Y., Cheng Y., Guo Y., Khudyakov I., Liu F., He P., Song Z., Li Z., Gao Y., Ang E.L., Zhao H., Zhang Y., Zhao S.
DNA modifications vary in form and function but generally do not alter Watson-Crick base pairing. Diaminopurine (Z) is an exception because it completely replaces adenine and forms three hydrogen bonds with thymine in cyanophage S-2L genomic DNA. However, the biosynthesis, prevalence, and importan ... >> More
DNA modifications vary in form and function but generally do not alter Watson-Crick base pairing. Diaminopurine (Z) is an exception because it completely replaces adenine and forms three hydrogen bonds with thymine in cyanophage S-2L genomic DNA. However, the biosynthesis, prevalence, and importance of Z genomes remain unexplored. Here, we report a multienzyme system that supports Z-genome synthesis. We identified dozens of globally widespread phages harboring such enzymes, and we further verified the Z genome in one of these phages, <i>Acinetobacter</i> phage SH-Ab 15497, by using liquid chromatography with ultraviolet and mass spectrometry. The Z genome endows phages with evolutionary advantages for evading the attack of host restriction enzymes, and the characterization of its biosynthetic pathway enables Z-DNA production on a large scale for a diverse range of applications. << Less
Science 372:512-516(2021) [PubMed] [EuropePMC]
This publication is cited by 8 other entries.