Studies on transfer ribonucleic acids and related compounds. XXVII. Linear and cyclic oligonucleotides obtained by polymerization of protected ribonucleoside 3'-phosphates.

Markham, A.F.; Nakagawa, Eiko; Ohtsuka, Eiko; Ikehara, Morio

doi:10.1248/cpb.27.2988

Cited by 4 publications

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“…The yield was 5.2 g (4.17 mmol), 83%. 2'-O-Benzoyl-3'-0-(o-nitrobenzyl)-N-benzoyladenosine (8) 7 (3.0 g, 4.0 mmol) was treated with benzoic anhydride (4.5 g, 20 mmol) in pyridine (600 ml) at room temperature for 18 hr, checked by TLC (30:1) (Rf 0.24-0.58), poured into ice water, then concentrated. The residue was coevaporated with toluene to remove pyridine, treated with 80% acetic acid (200 ml) in chloroform (20 ml) at room temperature for 2 hr, concentrated to dryness with coevaporation of aqueous ethanol and purified by chromatography on silica gel (200 g).…”

Section: Polymerization Of 2 Using DCCmentioning

confidence: 99%

“…For a large scale preparation of 2-5A, we have employed the triester approach to prepare the 5'-phosphorylated trinucleotide (3b, n=2) using monomer units (7,8,10) as shown in Chart 2. The nucleotide (7) was reacted with the nucleoside (8) using mesitylenesulfonyl triazolide (MST) as the activating reagent to yield the dinucleoside monophosphate which was isolated after removal of the 5'-monomethoxytrityl group by chromatography on silica gel in a yield of 86%.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of 5′-triphosphoryl 2′-5′ oligoadenylates (2-5A), and a general method for synthesis of 3′, 5′-bisphosphorylated oligonucleotides

et al. 1981

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2'-5'-Linked oligoadenylic acid 5'-triphosphates (2-5A) having chain lengths of 2-4 have been synthesized by polymerization of 3'-O-(o-nitrobenzyl)-N-benzoyladenosine 5'-phosphate followed by 5'-triphosphorylation via the imidazolidates. A large scale preparation of 5'-O-phosphoryladenylyl-(2'-5')-adenylyl-(2'-5')-adenosine was performed by the phosphotriester method using 5'-O-monomethoxytrityl-3'-O-(o-nitrobenzyl)-N-benzoyladenosine 2'-O-p-chlorophenylphosphate and 5'-O-phosphorodianilido-3'-O-(o-nitrobenzyl)-N-benzoyladenosine 2'-O-p-chlorophenylphosphate as intermediates. The trimer was also triphosphorylated by the imidazolide method. CD spectra for 5'-mono and triphosphorylated 2'-5' adenylates were measured as well as their UV hypochromicities. This triester method was also applied to the synthesis of 3',5'-bisphosphorylated protected oligoadenylic acids with natural 3'-5' linkages which could be used for further condensations to yield 5'-phosphorylated polynucleotides.

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Section: Polymerization Of 2 Using DCCmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of 5′-triphosphoryl 2′-5′ oligoadenylates (2-5A), and a general method for synthesis of 3′, 5′-bisphosphorylated oligonucleotides

et al. 1981

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Short Optimally Capped Duplex DNA as Conformationally Restricted Analogue of B‐DNA

Bannwarth

Dorn

Iaiza

et al. 1994

Helvetica Chimica Acta

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We describe the synthesis of short double-stranded DNA fragments (see 4 and 13) which are capped on both ends by an optimally designed linker molecule. The new structures are stable with respect to hybrid dissociation and should have implications in physical studies involving double-stranded DNA as well as in the antisense area for the specific modulation of gene expressions.1. Introduction. -Physical studies on DNA and DNA complexes with proteins/peptides or small molecules are mainly performed on oligonucleotide duplexes in order to decrease complexity. A drawback with oligonucleotides is that they often show a dynamic behavior with respect to hybridization, oligomer formation, and stem loop structures. One way to overcome these limitations is by cross-linking the two single-stranded DNA fragments. This may be achieved oiu internal disulfide cross-links, but this approach might disturb the instrinsic properties of the oligonucleotide double strand [ 11. Another possible solution is cyclic DNA with a complementary region. However, this creates dumbbell-like structures with loop formation on both sides adjacent to the complementary region thus hampering optimal hybridization [2] [3] (Fig. l a ) . A recently described stabilization of duplex DNA makes use of a hairpin structure which is cross-linked at the end by a disulfide bridge [4].

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Cordycepin analogues of 2-5A and its derivatives. Chemical synthesis and biological activity.

Sawai¹,

Imai²,

Lesiak³

et al. 1983

Journal of Biological Chemistry

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Studies on transfer ribonucleic acids and related compounds. XXVII. Linear and cyclic oligonucleotides obtained by polymerization of protected ribonucleoside 3'-phosphates.

Cited by 4 publications

References 0 publications

Synthesis and properties of 5′-triphosphoryl 2′-5′ oligoadenylates (2-5A), and a general method for synthesis of 3′, 5′-bisphosphorylated oligonucleotides

Synthesis and properties of 5′-triphosphoryl 2′-5′ oligoadenylates (2-5A), and a general method for synthesis of 3′, 5′-bisphosphorylated oligonucleotides

Short Optimally Capped Duplex DNA as Conformationally Restricted Analogue of B‐DNA

Cordycepin analogues of 2-5A and its derivatives. Chemical synthesis and biological activity.

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