Studies on transfer ribonucleic acids and related compounds. XXVI. Circular dichroic properties of cyclic oligoribonucleotides and their linear counterparts

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

doi:10.1002/bip.1980.360190207

Cited by 10 publications

(8 citation statements)

References 16 publications

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“…[6. 71 Here we show that 1 reacts smoothly with [Pt(PPh,)2C2H4] 2 to give the 1,3-distanna-2-platina [3]ferrocenophane 3 by oxidative addition accompanied by liberation of ethene (Scheme 1, route (a)). The molecular structure of 3 is…”

Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 82%

“…shown in Figure 1 .Is1 A related complex, 1,3-digerma-2-platina- [3]ferrocenophane Fe(C,H,GeMe,),[Pt(dppe)], has just recently been reported. ['] (twist angle z = 17").…”

Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 99%

“…The structure of the complexes 4 in solution follows unambiguously from the consistent set of NMR data (see Experimental Section). The reaction between 1 and 2 enabled us to determine structural and dynamic properties of 3, the first 1,3-distanna-2-platina [3]ferrocenophane, and the first fully characterized intermediate of a metal-catalyzed distannylation reaction. The novel 1,4-distanna[4]ferrocenophanes 4 are attractive compounds for further transformations because of their reactive Sn-C bonds.…”

Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 99%

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The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

Herberhold

Steffl

Milius

et al. 1997

Angew. Chem. Int. Ed. Engl.

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HPLC profiles of all the crude oligonucleotides is a major peak (typically more than 80-90% of the total integrated area) accompanied by some smalf impurities. The reason for such elevated purity is that the noncyclized chains, which are anchored to the support through a phosphate diester bond, are not cleaved from the resin upon oximate treatment, whereas the cyclic molecules linked through a phosphate triester are easily removed. Furthermore, neither the capped sequences nor the polymeric products formed by interchain reactions during cyclization are detached from the polymer. As a result, the main impurities that accompany the CON on the solid support are separated in the filtration step following oximate treatment.This reasoning accounts for the homogeneity of the crude products but also provides an argument for the cyclic character of the isolated oligonucleotides (major peaks). Moreover, their structures have been confirmed by two enzymatic digestion analyses. Complete degradation with snake-venom phosphodiesterase and alkaline phosphatase gives the expected ratio of nucleosides. On the other hand, the synthesized CONS show an increased resistance to degradation with calf-spleen phosphodiesterase under standard conditions, which is complete for the smallest sequences (up to a 12-mer) but decreases as the size of the molecule increases.["] Most of the CONS were also analyzed by mass spectrometry, either negative electrospray or MALDI-TOF or both, and show the expected mass.This simple procedure yields fairly pure products and, with regard to size, allows the limit under which template approaches are no longer efficient to be reached. The method is also amenable to scale-up, and, in fact, some products have been prepared on milligram scales for structural and biological studies. Experimental Section2: A solution of 1 (4 g) in AcOEt (130 mL) was slowly added to a solution of 2,4,5-trichlorophenoI (4.7 g) and dicyclohexylcarbodiimide (DCC, 4.9 g) in CH,CI, (22 mL), and the reaction mixture stirred overnight. The filtrate was washed with aqueous NaHCO, and dried, and the solvent removed under vacuum. The resulting oil was purified by chromatography over silica gel eluting with hexanes and increasing amounts of CH,CI,. After precipitation with hexanes 2.8 g of 2 were isolated (34% yield): m.p. =78"C; 'HNMR (200MHz, CDCI,): 6 =7.53, 7.26 (Cl,Ar), 7.35 (d), 7.20 (dd), 7.03 (d, CIAr), 5.60 (OH), 3.82 (CH,); EI-MS: m/z = 366. 3. A solution of tetrarole (0.23 mmol) in dry CH,CN (0.7 mL) was stirred with 5'-0-DMT-nucleoside phosphoramidite (0.23 mmol) and 2 (0.21 mmol) dissolved in CH,CI, (1.7 mL) under an argon atmosphere for 1 h. tBuOOH (0.24 mL, 3~ in toluene) was added, and 10 min later the reaction mixture diluted with CH,CI, and washed with water. The organic phase was dried, concentrated, and precipitated over hexanes. The products were isolated as white foams (65-75 % yield) and used without further purification. 3iP NMR (CDCI,): 6 = ca. -7.8(3a), ca. -10.5 (3b). 4. The amino support (ca. 1 mmol NH, groups) wa...

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Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 82%

“…shown in Figure 1 .Is1 A related complex, 1,3-digerma-2-platina- [3]ferrocenophane Fe(C,H,GeMe,),[Pt(dppe)], has just recently been reported. ['] (twist angle z = 17").…”

Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 99%

Section: Dedicated To Professor Cornelius G Kreiter On the Occasion mentioning

confidence: 99%

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The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

Herberhold

Steffl

Milius

et al. 1997

Angew. Chem. Int. Ed. Engl.

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“…The key intermediates 14, 15 and 18 were prepared from the 2'-0-(o-nitrobenzyl)adenosine derivatives (13). The phosphodiester (14) which served as the internal unit was obtained by phosphorylation with p-chlorophenyl phosphorotriazolide.11 The 3'-terminal unit (15) Chromatography of (5a, n=2) on a column of DEAE-cellulose (bicarbonate). Conditions for elution were the same as described in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…The dimer(19) was obtained by condensation of 15 and 18 using MST as the condensing reagent followed by separation using-silica gel. For the synthesis of the trimer (21), the 3'-unit (15) was condensed with the 5'-monomethoxytritylated compound (14) to obtain the intermediate (20) which was then elongated in the 5'-direction by reacting with the bis-phosphorylated nucleotide (18). The fully protected trimer (21) was isolated by chromatography on silica gel and characterized at each stage of deblocking.…”

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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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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Circular Dichroism and Its Empirical Application to Biopolymers

Johnson

1985

Methods of Biochemical Analysis

169

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Studies on transfer ribonucleic acids and related compounds. XXVI. Circular dichroic properties of cyclic oligoribonucleotides and their linear counterparts

Cited by 10 publications

References 16 publications

The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

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

Circular Dichroism and Its Empirical Application to Biopolymers

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Studies on transfer ribonucleic acids and related compounds. XXVI. Circular dichroic properties of cyclic oligoribonucleotides and their linear counterparts

Cited by 10 publications

References 16 publications

The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt0‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt0‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

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

Circular Dichroism and Its Empirical Application to Biopolymers

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The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds

The First 1,3‐Distanna‐2‐platina‐[3] ferrocenophane and the Pt⁰‐Catalyzed Addition of 1, 1, 2, 2,‐Tetramethyl‐1, 2‐distanna‐[2] ferrocenophane to CC Bonds