{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T08:37:29Z","timestamp":1785400649705,"version":"3.56.0"},"reference-count":42,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T00:00:00Z","timestamp":1741824000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T00:00:00Z","timestamp":1741824000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2025,3,3]]},"published-print":{"date-parts":[[2025,4,1]]},"abstract":"<jats:p>\n                    Isoguanine nucleosides constructed by different heterocyclic skeletons play a significant role in the context of genetic code expansion, as well as for purine\u2013purine base pairing. However, with respect to structure analysis, only limited information is available on this class of nucleosides. In this study, the single-crystal X-ray structure of 8-ethynyl-2\u2032-deoxyisoguanosine, C\n                    <jats:sub>12<\/jats:sub>\n                    H\n                    <jats:sub>13<\/jats:sub>\n                    N\n                    <jats:sub>5<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    \u00b7C\n                    <jats:sub>12<\/jats:sub>\n                    H\n                    <jats:sub>13<\/jats:sub>\n                    N\n                    <jats:sub>5<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    \u00b72H\n                    <jats:sub>2<\/jats:sub>\n                    O (\n                    <jats:bold>1<\/jats:bold>\n                    ), has been investigated. In the crystal of\n                    <jats:bold>1<\/jats:bold>\n                    , the N1-H and N3-H tautomers exist together. They are connected by O3\u2032\u2014H to O3\u2032 hydrogen bonds. The conformation at the glycosylic bond is\n                    <jats:italic>syn<\/jats:italic>\n                    for both tautomeric forms. This conformation is stabilized by intramolecular hydrogen bonds from N3 or N3\u2014H of the pyrimidine ring to the 5\u2032-OH group of the sugar residue. For both tautomers, the sugar conformation adopts a C2\u2032-\n                    <jats:italic>endo<\/jats:italic>\n                    \u2013C3\u2032-\n                    <jats:italic>exo<\/jats:italic>\n                    twist (\n                    <jats:sup>2<\/jats:sup>\n                    <jats:italic>T<\/jats:italic>\n                    <jats:sub>3<\/jats:sub>\n                    ;\n                    <jats:italic>S<\/jats:italic>\n                    -type), with\n                    <jats:italic>P<\/jats:italic>\n                    = 165.0 and 163.9\u00b0. A synclinal orientation is observed around the C4\u2014C5\u2032 bond. Crystal packing is controlled by a tridentate purine\u2013purine pair of 8-ethynyl-2\u2032-deoxyisoguanosine that is enabled by a tautomeric shift of the proton from N1 to N3 of the nucleobase. Additional stability to the 3D network is contributed by water molecules connecting different layers in the solid state. A Hirshfeld surface analysis was performed confirming the existence of the purine\u2013purine pair and the impact of the water molecules on hydrogen bonding. To the best of our knowledge, this is the first X-ray analysis on a nucleoside with two different tautomeric forms in the crystal unit that form a purine\u2013purine base pair.\n                  <\/jats:p>","DOI":"10.1107\/s2053229625001998","type":"journal-article","created":{"date-parts":[[2025,3,10]],"date-time":"2025-03-10T12:01:09Z","timestamp":1741608069000},"page":"230-237","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["8-Ethynyl-2\u2032-deoxyisoguanosine with two tautomeric forms in the unit cell: crystal structure, packing and Hirshfeld surface analysis"],"prefix":"10.1107","volume":"81","author":[{"given":"Dasharath","family":"Kondhare","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00wk05f95","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simone","family":"Budow-Busse","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00wk05f95","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6709-3673","authenticated-orcid":true,"given":"Constantin G.","family":"Daniliuc","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Leonard","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00wk05f95","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,3,13]]},"reference":[{"key":"vp3042_bb1","doi-asserted-by":"crossref","first-page":"8205","DOI":"10.1021\/ja00778a043","volume":"94","author":"Altona","year":"1972","journal-title":"J. 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