{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T04:44:44Z","timestamp":1786164284816,"version":"build-2736575974"},"reference-count":75,"publisher":"Wiley","issue":"29","license":[{"start":{"date-parts":[[2025,11,27]],"date-time":"2025-11-27T00:00:00Z","timestamp":1764201600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,11,27]],"date-time":"2025-11-27T00:00:00Z","timestamp":1764201600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2026,8,7]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Syntheses and base pairing properties of halogenated and nonhalogenated hypoxanthine nucleosides with 8\u2010aza\u20107\u2010deazapurine skeleton (dI*) are reported. Modified hypoxanthine nucleosides were accessed from 6\u2010alkoxy precursors. Single\u2010crystal X\u2010ray analyses disclosed unit cells consisting of two conformers adopting high\u2010anti conformation around the glycosylic bond with N\u2010type C3\u2019\u2010endo (3T2) or E\u2010type, O4\u2019\u2010endo (0E) sugar puckering. Crystal packing is stabilized by inosine\/inosine wobble base pairs as well as intermolecular and intramolecular hydrogen bonds. Hirshfeld surface analyses confirmed these findings. Halogenated and nonhalogenated dI* nucleosides were converted to phosphoramidites and applied to solid\u2010phase oligonucleotide synthesis. Single and consecutive incorporations were accomplished and Watson\u2013Crick and purine\u2013purine base pairing was investigated. Single incorporations opposite to canonical nucleosides afforded stable duplexes in all cases. T\n                    <jats:sub>m<\/jats:sub>\n                    values revealed the following order of stability dI*\u2010dC = dI*\u2010dA &gt; dI*\u2010dT &gt; dI*\u2010dG. Consecutive incorporations furnished more distinguished results. Double helices with halogenated dI*\u2010dC base pairs were the most stable ones, whereas hybridization for dI* opposite to dT was hindered. Halogenated dI*\u2010dG and dI*\u2010dA purine\u2010purine base pairs gave stable duplexes, whereas hybridization of nonhalogenated dI*\u2010dA pairs failed. From CD spectra, helical changes for duplexes with three dI*\u2010dG purine\u2010purine base pairs were detected. All other duplexes showed the typical shape of a B\u2010DNA.\n                  <\/jats:p>","DOI":"10.1002\/chem.202503204","type":"journal-article","created":{"date-parts":[[2025,11,28]],"date-time":"2025-11-28T07:54:29Z","timestamp":1764316469000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Halogenated Hypoxanthine 2'\u2010Deoxyribonucleosides With Pyrazolo[3,4\u2010\n                    <i>d<\/i>\n                    ]Pyrimidine Skeleton: Synthesis, Crystal Structures, Physical Properties, and Impact on Watson\u2010Crick and Purine\u2010Purine Base Pairs"],"prefix":"10.1002","volume":"32","author":[{"given":"Dasharath","family":"Kondhare","sequence":"first","affiliation":[{"name":"Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology  M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simone","family":"Budow\u2010Busse","sequence":"additional","affiliation":[{"name":"Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology  M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Constantin","family":"Daniliuc","sequence":"additional","affiliation":[{"name":"Organisch\u2010Chemisches Institut Universit\u00e4t M\u00fcnster  M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Leonard","sequence":"additional","affiliation":[{"name":"Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology  M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,27]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/genes12040600"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.omtn.2024.102284"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.gde.2014.07.008"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022\u20102836(66)80022\u20100"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/263289a0"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021\u20109258(18)89400\u20105"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/263285a0"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra41492b"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/29.12.2437"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2004.09.024"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/28.17.3224"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/22.20.4039"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB01478B"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/369492a0"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(02)00888\u20102"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01746"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3030388"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1080\/15257779508012532"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.7b08825"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/28.15.2911"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198519850707"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1080\/15257779908043087"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1522\u20102675(19990113)82:1<12::AID\u2010HLCA12>3.0.CO;2\u2010L"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200890131"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1093\/nass\/nrn239"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270108019835"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00240a006"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00125a009"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200590052"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1080\/15257770008045448"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/23.13.2499"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1124\/pr.58.1.6"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jbc.2023.105189"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.07.027"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00074a024"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0MD00227E"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24050983"},{"key":"e_1_2_8_39_1","first-page":"165","article-title":"Methods in Molecular Biology, in 'Oligonucleotide Synthesis: Methods and Applications', Ed. P. Herdewijn","volume":"288","author":"Seela F.","year":"2004","journal-title":"Humana Press Inc"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c02646"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.2c00584"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/29.10.2069"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202501227"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)91106\u20102"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19850680305"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1080\/07328318708056253"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/14.4.1825"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1080\/15257770.2013.806661"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1135\/cccc20060769"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.21.1143"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19811140505"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1039\/a804706e"},{"key":"e_1_2_8_53_1","first-page":"9","article-title":"IUPAC\u2010IUB Joint Commission on Biochemical Nomenclature, Abbreviations and Symbols for the Description of Conformations of Polynucleotide Chains","volume":"131","year":"1983","journal-title":"European Journal of Biochemistry"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270104032123"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00723a032"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00778a043"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/28.18.3625"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo010299j"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4612-5190-3"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/j150576a013"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0567740873004152"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1039\/B818330A"},{"key":"e_1_2_8_63_1","author":"Turner M. J.","year":"2017","journal-title":"Crystal Explorer 17"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1111\/febs.13307"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.4c00982"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202005199"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c01370"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/14.19.7727"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/17.1.55"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/15.19.7935"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/20.18.4753"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi9615710"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05042"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021\u20109258(18)48187\u20102"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/19.19.5263"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22064"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202503204","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202503204","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202503204","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T04:35:08Z","timestamp":1786163708000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202503204"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,27]]},"references-count":75,"journal-issue":{"issue":"29","published-print":{"date-parts":[[2026,8,7]]}},"alternative-id":["10.1002\/chem.202503204"],"URL":"https:\/\/doi.org\/10.1002\/chem.202503204","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,11,27]]},"assertion":[{"value":"2025-10-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e03204"}}