A Conformationally Preorganized Universal Solid Support for Efficient Oligonucleotide Synthesis

Guzaev, Andrei; Manoharan, Muthiah

doi:10.1021/ja0284613

Cited by 39 publications

(30 citation statements)

References 4 publications

(4 reference statements)

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“…Starting the synthesis of a new oligonucleotide sequence on the 5′-terminal OH position of another oligonucleotide sequence is not difficult. These sites are similar to the surfaces of underivatized universal (36,37) or reusable (38) solid-phase supports, which contain hydroxyl linker arms. However, the linkage to each new oligonucleotide's starting point (the 3′-nucleoside) must be cleavable.…”

Section: Resultsmentioning

confidence: 97%

Tandem oligonucleotide synthesis using linker phosphoramidites

Pon

2005

Nucleic Acids Research

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Multiple oligonucleotides of the same or different sequence, linked end-to-end in tandem can be synthesized in a single automated synthesis. A linker phosphoramidite [R. T. Pon and S. Yu (2004) Nucleic Acids Res., 32, 623–631] is added to the 5′-terminal OH end of a support-bound oligonucleotide to introduce a cleavable linkage (succinic acid plus sulfonyldiethanol) and the 3′-terminal base of the new sequence. Conventional phosphoramidites are then used for the rest of the sequence. After synthesis, treatment with ammonium hydroxide releases the oligonucleotides from the support and cleaves the linkages between each sequence. Mixtures of one oligonucleotide with both 5′- and 3′-terminal OH ends and other oligonucleotides with 5′-phosphorylated and 3′-OH ends are produced, which are deprotected and worked up as a single product. Tandem synthesis can be used to make pairs of PCR primers, sets of cooperative oligonucleotides or multiple copies of the same sequence. When tandem synthesis is used to make two self-complementary sequences, double-stranded structures spontaneously form after deprotection. Tandem synthesis of oligonucleotide chains containing up to six consecutive 20mer (120 bases total), various trinucleotide codons and primer pairs for PCR, or self-complementary strands for in situ formation of double-stranded DNA fragments has been demonstrated.

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Section: Resultsmentioning

confidence: 97%

Tandem oligonucleotide synthesis using linker phosphoramidites

Pon

2005

Nucleic Acids Research

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“…In our earlier communication, [21,22] we proposed a novel universal linker molecule 1 for efficient synthesis of high quality oligonucleotides ( Figure 1). By design this molecule contains a cyclic anhydride and on loading to an amino-derivatized solid support such as CPG or GE's PS200 Primer Support undergoes ring opening to liberate a free carboxyl group, which is subsequently capped by reacting with n-propyl amine in presence of HBTU.…”

Section: Synthesis Of Universal Linker and Loading To Solid Supportmentioning

confidence: 99%

A Novel Universal Linker for Efficient Synthesis of Phosphorothioate Oligonucleotides

Wang

Olsen

Ravikumar

2007

Nucleosides, Nucleotides and Nucleic Acids

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A versatile and conformationally preorganized universal linker molecule is reported here for efficient synthesis of phosphorothioate oligonucleotides. With respect to nucleoside loaded support, comparable yield and quality based on ion-pair LC-MS are obtained for both deoxy and 2'-O-methoxyethyl modified phosphorothioate oligonucleotides. No 3'-phosphate or phosphorothioate monoester or any modification of universal molecule still attached to oligonucleotide was observed. [structure: see text]

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“…In all cases, basic conditions are required for the cleavage of the final product via the intramolecular cyclization. 37 with a 1,2-cyclopentyl moiety [147], 38 derived from 3-amino-1,2-propanediol [148], and a conformationally preorganized universal linker 39 [149] have been reported.…”

Section: Solid Supports and Linkersmentioning

confidence: 99%

Strategies Useful for the Chemical Synthesis of Oligonucleotides and Related Compounds

Tsukamoto¹,

Hayakawa²

2005

Frontiers in Organic Chemistry

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This review summarizes recent progress in useful strategies for the chemical synthesis of nucleic acids and related compounds surrounding the core of present author's works. Among the methods employed for internucleotide-bond formation, the phosphoramidite method is superior in many respects, including coupling efficiency, stability of building blocks, ease of automation, purity of the product, and synthetic applicability. The original phosphoramidite method has several drawbacks, and thus a great amount of effort has been focused on the development of promoters for internucleotide-bond formation, oxidation of the phosphite intermediate, protecting groups, and linkers and solid supports in order to broaden the synthetic applicability of this extremely useful method. The author's work to date, including the development of acid/azole complexes as promoters, anhydrous/non-basic oxidation methods, an AOC/allyl-protected strategy, will be highlighted, together with a discussion of the applicability of these methods for the synthesis of biologically important compounds.

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A Conformationally Preorganized Universal Solid Support for Efficient Oligonucleotide Synthesis

Cited by 39 publications

References 4 publications

Tandem oligonucleotide synthesis using linker phosphoramidites

Tandem oligonucleotide synthesis using linker phosphoramidites

A Novel Universal Linker for Efficient Synthesis of Phosphorothioate Oligonucleotides

Strategies Useful for the Chemical Synthesis of Oligonucleotides and Related Compounds

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