Functionalization of the sugar moiety of oligoribonucleotides on solid support.
A solid-phase method for the introduction of a variety of different side chains into oligoribonucleotides is presented. It is based on a beta-D-allofuranosyl phosphoramidite with a bromopentyl-substituent tethered to the 6'-O position. After its incorporation into fully protected, immobilized RNA sequences, the bromine was substituted with a variety of soft nucleophiles which, in some cases, allowed further transformations. After deprotection and detachment, the corresponding functionalized oligoribonucleotides were purified and characterized. Incorporation of such side chains led to a slight lowering of transition temperatures, but some of them led to a significant enthalpic stabilization of an A-type RNA duplex.
Wu
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Organisch-chemisches Laboratorium der Eidgenössischen Technischen Hochschule, Universitätstrasse 16, CH-8092 Zürich, Switzerland.
Pitsch
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D000577:Amides / Q000737:chemistry; D001483:Base Sequence; D001966:Bromine / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003596:Cytosine / Q000031:analogs & derivatives / Q000737:chemistry; D004355:Drug Stability; D006001:Glycoconjugates / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D009843:Oligoribonucleotides / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D013816:Thermodynamics
D000577:Amides; D006001:Glycoconjugates; D009843:Oligoribonucleotides; D010756:Phosphoric Acids; C115333:allofuranosyl cytosine; D012313:RNA; D003596:Cytosine; C011067:phosphoramidic acid; D001966:Bromine