The preparation and application of functionalised synthetic oligonucleotides: III. Use of H-phosphonate derivatives of protected amino-hexanol and mercapto-propanol or-hexanol
Open Access
- 1 January 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 16 (6) , 2659-2670
- https://doi.org/10.1093/nar/16.6.2659
Abstract
Syntheses of H-phosphonate salts (4a-e) of N / S-protected alcohols such as 6-aminohexan-1-ol, 3-mercaptopropan-1-ol and 6-mercaptohexan-1-ol are described using 2-chloro-5,6-benzo-1,3,2-phosphorin-4-one (2) as the phosphonylating agent. The H-phosphonate salts (4a-e), in the presence of pivaloyl chloride or adamantoyl chloride as an activator, were coupled to the 5′-end of synthetic oligonucleotides on solid supports to produce amino or thio-linked oligonucleotides. Following deprotection and purification, fluorescent dyes, biotin derivatives and poly-L-lysine-maleimide were separately attached to the functionalised oligonucleotides. Identical derivatized oligomers were obtained with cyanoethyl-N,N-diisopropylamidite chemistry and amidites (5a-e) of the respective alcohols.This publication has 21 references indexed in Scilit:
- Synthesis and application of derivatizable oligonucleotidesNucleic Acids Research, 1987
- Structural junctions in DNA: the influence of flanking sequence on nuclease digestion specificitiesNucleic Acids Research, 1985
- Non-radioactive hybridization probes prepared by the chemical labelling of DNA and RNA with a novel reagent, photobiotinNucleic Acids Research, 1985
- Biotin-labeled synthetic oligodeoxyribonucleotides: chemical synthesis and uses as hybridization probesNucleic Acids Research, 1985
- The synthesis of oligonucleotides containing an aliphatic amino group at the 5′ terminus: synthesis of fluorescent DNA primers for use in DNA sequence analysisNucleic Acids Research, 1985
- Polymer support oligonucleotide synthesis XVIII1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final productNucleic Acids Research, 1984
- Biotin-Labeled Oligonucleotides: Enzymatic Synthesis and Use as Hybridization ProbesDNA, 1984
- Biotin and fluorescent labeling of RNA using T4 RNA ligaseNucleic Acids Research, 1983
- Rapid and sensitive colorimetric method for visualizing biotin-labeled DNA probes hybridized to DNA or RNA immobilized on nitrocellulose: Bio-blots.Proceedings of the National Academy of Sciences, 1983
- Irreversible coupling of immunoglobulin fragments to preformed vesicles. An improved method for liposome targeting.Journal of Biological Chemistry, 1982