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dc.contributor.authorGarland, PBen_US
dc.contributor.authorSerafinowski, PJen_US
dc.date.accessioned2018-08-30T08:13:56Z
dc.date.issued2009en_US
dc.identifier3en_US
dc.identifier.citationORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 pp. 451 - 459en_US
dc.identifier.issn1477-0520en_US
dc.identifier.urihttps://repository.icr.ac.uk/handle/internal/2413
dc.identifier.doi10.1039/b813319ken_US
dc.description.abstractConventional solid-phase oligonucleotide synthesis overcomes the reversibility of acid-dependent detritylation by washing away the released dimethoxytrityl cations (DMT(+)) with acid. This option is unavailable if the acid is photogenerated in an overlying solid film, as in the photolithographic fabrication of oligonucleotide arrays on planar surfaces. To overcome the resulting reversibility problem we developed methods of achieving >= 98% detritylation of glass-attached 5’-O-DMT-thymidine, a model for 5’-O-DMT-protected oligonucleotides, by the photogeneration of trichloroacetic acid in a solid film. Enhanced intrafilm diffusion, insufficient to degrade the photolithographic resolution but enabling DMT(+) to move from its plane of release into the overlying photoacid-generating film, increased detritylation from <= 30% to >= 98%. Inclusion of an intrafilm carbocation scavenger such as a triarylsilane hydride converted the detritylation into a time-dependent irreversible process proceeding to >= 99% detritylation within 60 s following brief photoacid generation. Light sensitivity is high, exceeding direct photodeprotection methods by 15-100 fold.en_US
dc.format.extent451 - 459en_US
dc.languageEnglishen_US
dc.language.isoEnglishen_US
dc.publisherROYAL SOC CHEMISTRYen_US
dc.titleHigh yield detritylation of surface-attached nucleosides with photoacid generated in an overlying solid film: roles of translational diffusion and scavengingen_US
dc.typeJournal Article
rioxxterms.versionofrecord10.1039/b813319ken_US
rioxxterms.licenseref.startdate2009en_US
rioxxterms.typeJournal Article/Reviewen_US
dc.relation.isPartOfORGANIC & BIOMOLECULAR CHEMISTRYen_US
pubs.notesaffiliation: Garland, PB (Reprint Author), Inst Canc Res, Sect Mol Carcinogenesis, Sutton SM2 5NG, Surrey, England. Garland, Peter B., Inst Canc Res, Sect Mol Carcinogenesis, Sutton SM2 5NG, Surrey, England. Serafinowski, Pawel J., Inst Canc Res, Canc Res UK Ctr Canc Therapeut, Sutton SM2 5NG, Surrey, England. keywords-plus: CHEMICAL SYNTHESIS; SILYL CATIONS; DNA; OLIGONUCLEOTIDES; HYBRIDIZATION research-areas: Chemistry web-of-science-categories: Chemistry, Organic author-email: [email protected] [email protected] funding-acknowledgement: Leverhulme Trust; BBSRC and EPSRC [EGM16064]; Institute of Cancer Research funding-text: This work was supported by grants from the Leverhulme Trust, the BBSRC and EPSRC jointly through Grant No. EGM16064, and the Institute of Cancer Research. We also thank Professor Colin Cooper for his encouragement and support. number-of-cited-references: 28 times-cited: 5 usage-count-last-180-days: 0 usage-count-since-2013: 3 journal-iso: Org. Biomol. Chem. doc-delivery-number: 397KU unique-id: ISI:000262662400008 da: 2018-08-29en_US
pubs.notesNot knownen_US
pubs.organisational-group/ICR
pubs.volume7en_US
pubs.embargo.termsNot knownen_US
dc.contributor.icrauthorGarland, Peteren_US
dc.contributor.icrauthorSerafinowski, Pawelen_US


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