title: Synthesis of peptide nucleic acid FRET probes via an orthogonally protected building block for post-synthetic labeling of peptide nucleic acids at the 5-position of uracil.
abstract: We report the design and synthesis of an orthogonally protected peptide nucleic acid (PNA) building block, Fmoc-PNA-U'-(Dde)-OH, and its use in the construction of PNA FRET probes. This building block allows for the post-synthetic attachment of reporter groups to the amino group attached to the 5-position of uracil (U) following selective deprotection of the Dde group. We illustrate the use of this building block for the synthesis of a series of FAM Cy5 donor acceptor pairs and their ability to detect a target DNA sequence.
authors.affiliation: Department of Chemistry, Washington UniversitySt Louis, Missouri 63130, USA.
authors.forename: Bereket Y
authors.initials: BY
authors.lastname: Oquare
authors.forename: John-Stephen
authors.initials: JS
authors.lastname: Taylor
mesh_terms: D001483:Base Sequence; D004247:DNA / Q000032:analysis / Q000235:genetics; D005449:Fluorenes / Q000737:chemistry; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D016372:RNA, Antisense / Q000235:genetics / Q000378:metabolism; D012333:RNA, Messenger / Q000235:genetics / Q000378:metabolism; D013194:Staining and Labeling; D014498:Uracil / Q000737:chemistry*
chemical_list: D005449:Fluorenes; D005456:Fluorescent Dyes; D020135:Peptide Nucleic Acids; D016372:RNA, Antisense; D012333:RNA, Messenger; D014498:Uracil; D004247:DNA