| High yield detritylation of surface-attached nucleosides with photoacid generated in an overlying solid film: roles of translational diffusion and scavenging. | |
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MedLine Citation:
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PMID: 19156309 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Conventional 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 >or=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 <or=30% to >or=98%. Inclusion of an intrafilm carbocation scavenger such as a triarylsilane hydride converted the detritylation into a time-dependent irreversible process proceeding to >or=99% detritylation within 60 s following brief photoacid generation. Light sensitivity is high, exceeding direct photodeprotection methods by 15-100 fold. |
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Authors:
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Peter B Garland; Pawel J Serafinowski |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-11-28 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 7 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2009 Feb |
Date Detail:
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Created Date: 2009-01-21 Completed Date: 2009-03-10 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 451-9 Citation Subset: IM |
Affiliation:
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Section of Molecular Carcinogenesis, The Institute of Cancer Research, Sutton, Surrey, UKSM2 5NG. peter@garland.org.uk |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Computer Simulation Diffusion* Kinetics Light Models, Chemical Nucleosides / chemistry* Photolysis* Plasticizers / chemistry Surface Properties Time Factors Trichloroacetic Acid / chemistry* Trityl Compounds / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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//Biotechnology and Biological Sciences Research Council |
| Chemical | |
Reg. No./Substance:
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0/Nucleosides; 0/Plasticizers; 0/Trityl Compounds; 7500-76-7/4,4'-dimethoxytrityl cation; 76-03-9/Trichloroacetic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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