The preparation and application of functionalised synthetic oligonucleotides: III. Use of H-phosphonate derivatives of protected amino-hexanol and mercapto-propanol or -hexanol.
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.
Sinha
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Chemistry Division, Biosearch Inc., San Rafael, CA 94901.
Cook
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RM
D000433:1-Propanol; D000605:Amino Alcohols; D001710:Biotin; D055598:Chemical Phenomena; D002621:Chemistry; D005456:Fluorescent Dyes; D000441:Hexanols; D009841:Oligonucleotides / Q000138:chemical synthesis; D063065:Organophosphonates; D013438:Sulfhydryl Compounds
D000605:Amino Alcohols; D005456:Fluorescent Dyes; D000441:Hexanols; D009841:Oligonucleotides; D063065:Organophosphonates; D013438:Sulfhydryl Compounds; D001710:Biotin; D000433:1-Propanol