d5SICS

{{chembox

|ImageFile1=D5SICS-skeletal.png

|ImageName1=Haworth projection of d5SICS

|ImageFile2=D5SICS.png

|ImageName2=Ball-and-stick model of d5SICS

|Name=d5SICS

|IUPACName = 2-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-methylisoquinoline-1(2H)-thione

|SystematicName = 2-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinoline-1(2H)-thione

|Section1= {{Chembox Identifiers

| CASNo = 1010689-00-5

| CASNo_Ref = {{Cascite|changed|ChemSpider}}

| SMILES = OCC3OC(N2C=Cc1cc(ccc1C2=S)C)CC3(O)

| ChemSpiderID = 58191598

| PubChem=102129314

| SMILES2 = Cc1ccc2c(c1)ccn(c2=S)[C@H]3C[C@@H]([C@H](O3)CO)O

| StdInChI = 1S/C15H17NO3S/c1-9-2-3-11-10(6-9)4-5-16(15(11)20)14-7-12(18)13(8-17)19-14/h2-6,12-14,17-18H,7-8H2,1H3/t12-,13+,14+/m0/s1

| StdInChIKey = ISOKBQJGUJTDAE-BFHYXJOUSA-N

}}

|Section2 = {{Chembox Properties

| Formula = C₁₅H₁₇NO₃S

| MolarMass = 291.37 g/mol

}}

}}

d5SICS is an artificial nucleoside containing 6-methylisoquinoline-1-thione-2-yl group instead of a base.

It pairs up with dNaM 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.{{cite web |url=http://www.rsc.org/chemistryworld/2014/05/bacterium-survives-unnatural-dna-transplant |title=Bacterium survives unnatural DNA transplant |newspaper=Rsc.org |date= |author= |accessdate= July 29, 2015}}{{cite journal |title=Efficient and sequence-independent replication of DNA containing a third base pair establishes a functional six-letter genetic alphabet |doi= 10.1073/pnas.1205176109 |volume=109 |year=2012 |journal=Proceedings of the National Academy of Sciences |pages=12005–12010 | last1 = Malyshev | first1 = D. A. |issue=30 |pmid=22773812 |pmc=3409741|bibcode=2012PNAS..10912005M |doi-access=free }} 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.{{cite journal |title=Structural Insights into DNA Replication Without Hydrogen-Bonds | doi=10.1021/ja409609j | journal=J Am Chem Soc | year=2013 | last1=Betz | first1=Karin | display-authors=etal| pmc=3982147 | pmid=24283923 | volume=135 | issue=49 | pages=18637–43}} The d5SICS-dNaM pairing replaced an older dNaM-dTPT3 pairing. {{cite news |url= https://www.washingtonpost.com/news/morning-mix/wp/2017/01/24/biologists-breed-life-form-with-lab-made-dna-dont-call-it-jurassic-park/ |title= Biologists breed life form with lab-made DNA. Don't call it 'Jurassic Park.' |author= Ben Guarino |newspaper= Washington Post |date= 24 January 2017 }}