dNaM

dNaM
Names
	IUPAC name (1R)-1,4-Anhydro-2-deoxy-1-(3-methoxy-2-naphthyl)-D-erythro-pentitol
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	58191600;
CompTox Dashboard (EPA)	DTXSID501046397 ;
	InChI InChI=1S/C16H18O4/c1-19-14-7-11-5-3-2-4-10(11)6-12(14)15-8-13(18)16(9-17)20-15/h2-7,13,15-18H,8-9H2,1H3/t13-,15+,16+/m0/s1 Key: XVSHFDVHYNHNDU-NUEKZKHPSA-N;
	SMILES COc1cc2ccccc2cc1[C@H]3C[C@@H]([C@H](O3)CO)O;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

dNaM is an artificial nucleoside containing a 3-methoxy-2-naphthyl group instead of a base.

It pairs up with d5SICS in a hydrophobic interaction. It was not able to be removed by the error-correcting machinery of the E. coli into which it was inserted.^[1]^[2] The pairing of d5SICS–dNaM is mediated by packing and hydrophobic forces instead of hydrogen bonding, which occurs in natural base pairs. Therefore, in free DNA, rings of d5SICS and dNaM are placed in parallel planes instead of the same plane.^[3]

References

^ "Bacterium survives unnatural DNA transplant". Rsc.org. Retrieved July 29, 2015.
^ "Efficient and sequence-independent replication of DNA containing a third base pair establishes a functional six-letter genetic alphabet". Pnas.org. Retrieved July 29, 2015.
^ Betz, Karin; et al. (2013). "Structural Insights into DNA Replication Without Hydrogen-Bonds". J Am Chem Soc. doi:10.1021/ja409609j. PMC 3982147.

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[MyUser_Rsc.org_July_29_2015c-1] "Bacterium survives unnatural DNA transplant". Rsc.org. Retrieved July 29, 2015.

[MyUser_Pnas.org_July_29_2015c-2] "Efficient and sequence-independent replication of DNA containing a third base pair establishes a functional six-letter genetic alphabet". Pnas.org. Retrieved July 29, 2015.

[3] Betz, Karin; et al. (2013). "Structural Insights into DNA Replication Without Hydrogen-Bonds". J Am Chem Soc. doi:10.1021/ja409609j. PMC 3982147.

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