dNaM

dNaM
Names
	IUPAC name (1R)-1,4-Anhydro-2-deoxy-1-(3-methoxy-2-naphthyl)-D-erythro-pentitol
Identifiers
CAS Number	1117893-19-2;
3D model (JSmol)	Interactive image;
ChemSpider	58191600;
PubChem CID	102129315;
	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.

When it was originally successfully introduced into DNA, it was paired up with dTPT3. For short it is called X whilst the dTPT3 being called Y.[1] dTPT3 was replaced by d5SICS in revised versions.[2] It pairs 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. While the E. coli managed to hold onto the new base for a short period and even reproduce, it eventually rejected it.[3][4] 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.[5]

References

Sarah Caplan (29 November 2017). "Cells with DNA made in lab lead to 'Holy Grail' of synthetic biology". The Washington Post.
Ben Guarino (24 January 2017). "Biologists breed life form with lab-made DNA. Don't call it 'Jurassic Park.'". Washington Post.
"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". Retrieved July 29, 2015. Cite journal requires |journal= (help)
Betz, Karin; et al. (2013). "Structural Insights into DNA Replication Without Hydrogen-Bonds". J Am Chem Soc. 135: 18637–43. doi:10.1021/ja409609j. PMC 3982147. PMID 24283923.

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[WashPost-20171129-1] Sarah Caplan (29 November 2017). "Cells with DNA made in lab lead to 'Holy Grail' of synthetic biology". The Washington Post.

[WashPost-20170124-2] Ben Guarino (24 January 2017). "Biologists breed life form with lab-made DNA. Don't call it 'Jurassic Park.'". Washington Post.

[MyUser_Rsc.org_July_29_2015c-3] "Bacterium survives unnatural DNA transplant". Rsc.org. Retrieved July 29, 2015.

[MyUser_Pnas.org_July_29_2015c-4] "Efficient and sequence-independent replication of DNA containing a third base pair establishes a functional six-letter genetic alphabet". Retrieved July 29, 2015. Cite journal requires |journal= (help)

[5] Betz, Karin; et al. (2013). "Structural Insights into DNA Replication Without Hydrogen-Bonds". J Am Chem Soc. 135: 18637–43. doi:10.1021/ja409609j. PMC 3982147. PMID 24283923.