Arylsulfonyl chlorides in the presence of N-methylimidazole as efficient condensing reagents in phosphotriester oligonucleotide synthesis

Ефимов, В. А.; Reverdatto, Sergey; Chakhmakcheva, O.G.

doi:10.1016/s0040-4039(00)86994-4

Cited by 65 publications

(10 citation statements)

References 7 publications

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“…As reported for erythrocyte proteolipids (35) and the myelin proteolipid (36), there is minimal overlap of protein and PL when the eluting chloroform/methanol is acidified (Fig. 1 [28][29][30][31][32][33][34][35][36] (Fig. 4, curve D).…”

Section: Resultsmentioning

confidence: 73%

“…Specific proteins may regulate these dynamic surface properties. The predominant surfactant protein is a well-characterized, lipid-associated glycoprotein, SP [28][29][30][31][32][33][34][35][36] Pulmonary surfactant is a lipid-rich material secreted as tightly packed lamellae into the extracellular alveolar fluid layer (1). Within the alveolar space, surfactant lipids are found in a number of different structural forms, including lamellar bodies, tubular myelin, and various vesicular structures (2).…”

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confidence: 99%

“…The predominant surfactant-associated protein is the glycoprotein (28)(29)(30)(31)(32)(33)(34)(35)(36) characterized by a collagenlike NH2-terminal domain and variable N-linked glycosylation of the COOH-terminal region (11)(12)(13). is water soluble but readily associates with phospholipids (PLs) (14).…”

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confidence: 99%

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Nucleotide and amino acid sequences of pulmonary surfactant protein SP 18 and evidence for cooperation between SP 18 and SP 28-36 in surfactant lipid adsorption.

Hawgood¹,

Benson²,

Schilling³

et al. 1987

Proc. Natl. Acad. Sci. U.S.A.

354

237

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Pulmonary surfactant is a lipid-rich material that promotes alveolar stability by lowering the surface tension at the air-fluid interface in the peripheral air spaces. The turnover of surfactant phospholipids in the alveolar space is fast, and several lines of evidence suggest there is rapid formation and replenishment of the phospholipid surface film during normal respiration. Specific proteins may regulate these dynamic surface properties. The predominant surfactant protein is a well-characterized, lipid-associated glycoprotein, SP [28][29][30][31][32][33][34][35][36] Pulmonary surfactant is a lipid-rich material secreted as tightly packed lamellae into the extracellular alveolar fluid layer (1). Within the alveolar space, surfactant lipids are found in a number of different structural forms, including lamellar bodies, tubular myelin, and various vesicular structures (2). Although the lipid compositions of the surfactant structures are similar, the physical properties, particularly the ability ofthe lipoprotein complexes to form a surface film, are quite different (3). Specific proteins appear to influence the structure and surface activity of surfactant-lipid complexes (4-10).The predominant surfactant-associated protein is the glycoprotein SP 28-36 (28-36 kDa) characterized by a collagenlike NH2-terminal domain and variable N-linked glycosylation of the COOH-terminal region (11-13). SP 28-36 is water soluble but readily associates with phospholipids (PLs) (14). In the presence of calcium, SP 28-36 causes PL aggregation and increases the rate of adsorption of surfactant lipids to an air-fluid interface (6,8,14). A second group of very hydrophobic proteins has been identified in lamellar bodies isolated from lung homogenate and in surfactant isolated from the bronchoalveolar wash (4, 9, 10, 15-17). Very little is known about the homogeneity, structure, or function ofthis group of hydrophobic proteins, but it has been reported that at least one of these proteins enhances PL surface film formation (9,10,18 (20). The surfactant in water (-16 mg of PL per ml, 2 mg of protein per ml) was extracted in 1-butanol (1:50, vol/vol) at room temperature (21). The surfactant/butanol mixture was spun twice at 10,000 X gav for 20 min to sediment the butanolinsoluble protein (94% of the total). The butanol supernatant was dried by rotary evaporation and the residue was resuspended in chloroform/methanol/0.1 M HCl, 1:1:0.5, vol/vol). A small amount of insoluble material was removed by centrifugation and the supernatant, containing 30 mg ofPL in 1 ml, was applied to a 1 cm x 45 cm column of Sephadex and eluted at 4 ml/hr with the same solvent at 40C. The eluted fractions, 0.5 ml, were assayed for protein (22) in the presence of 1% NaDodSO4, phosphorus (23) for the calculation of the PL content, and cholesterol (24). An aliquot of each fraction containing protein was analyzed by NaDodSO4/PAGE (25) and silver staining (26). 66The publication costs of this article were defrayed in part by page charge payment. This article...

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Section: Resultsmentioning

confidence: 73%

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confidence: 99%

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Nucleotide and amino acid sequences of pulmonary surfactant protein SP 18 and evidence for cooperation between SP 18 and SP 28-36 in surfactant lipid adsorption.

Hawgood¹,

Benson²,

Schilling³

et al. 1987

Proc. Natl. Acad. Sci. U.S.A.

354

237

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“…This test showed the complate digestion of both oligonucleotide by RNase T2. By measuring the amount of incorported [y-32 P] to 5'-hydroxyl group, the ratio of pA, pG, pC, pU obtained were 2.9:0:1.2:2.0 (theoretical, 3 ively. In the above reaction, the 3'-terminal nucleoside was not labeled by the polynucleotide kinase due to the lack of 3'-phosphate.…”

Section: Synthesis Of Oligoribonucleotidesmentioning

confidence: 97%

Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2′-hydroxyl via a phosphite triester approach

Tanaka¹,

Tamatsukuri²,

Ikehara³

1986

Nucl Acids Res

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The hepta and undecaribonucleotide were synthesized on a controlled pore glass beads using o-nitrobenzyl protection of 2'-hydroxyls via a phosphite approach. By using 5-p-nitrophenyltetrazole for the activation of nucleoside-phosphoramidite, the condensation reaction was carried out very rapidly (2.5 min). The time required for one cycle was only 16 min. The hepta-(UACUAAC) and undecaribonucleotides (GUAUGUUAAUA) were obtained in yields of 28 and 17% respectively from the original resin.

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“…Since an sp 2 -hybridized ring Natom reveals a similar activation power as a NO 2 group, the pyridinyl, pyrimidinyl, and pyrazinyl moieties were chosen as new entities in these investigations. Scheme 2 thymidine (37) to form, under 2,4,6-triisopropylbenzenesulfonyl chloride (TPS-Cl)/1methyl-1H-imidazole activation [20], the dinucleoside phosphotriesters 38 ± 41 in 67, 68, 77, and 74% yields, respectively. The corresponding dithymidinyl npe phosphotriester 42 was prepared according to [21] for comparative studies.…”

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confidence: 99%

Nucleotides, Part LXVI,β-Heteroarylethyl Groups - New Phosphate-Protecting Groups for Phosphotriester Chemistry

Reiner

Kvasyuk

Pfleiderer

2000

HCA

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The b-heteroaryl-substituted ethanols 6 ± 10 were synthesized and, together with pyridine-2-ethanols and pyridine-4-ethanols, were tested as a new type of phosphate-protecting groups in the synthesis of oligonucleotides by the phosphotriester approach. The synthesis of 5'-O-(monomethoxytrityl)thymidine 3'-(bheteroarylethyl 2,5-dichlorophenyl phosphates) 13 ± 17 and 21 provided useful monomeric building blocks in which the various blocking groups could be removed selectively by acid (MeOTr), oximate (2,5-dichlorophenyl phosphate), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (heteroarylethyl phosphate) treatment. The new, fully blocked dimers 38 ± 41, with b-heteroarylethyl protecting groups in the phosphate moiety, were synthesized. The b-heteroarylethyl groups show a broad range of stability towards base treatment in aprotic solvents depending upon the activation of the HÀC(b) atoms by the heterocyclic moiety.1. Introduction. ± The use of b-eliminating phosphate-protecting groups can be regarded as an important improvement in phosphotriester chemistry [2] since cleavage of the phosphotri-to the phosphodiester stage will proceed without nucleophilic attack at the P-atom, avoiding a potential breakdown of the internucleotidic linkage. Among those protecting groups are the b-cyanoethyl (ce) group [3], the methyl-substituted bcyanoethyl groups [4], and the b-(alkylsulfonyl)-and b-(arylsulfonyl)ethyl groups [5]. Since these blocking groups are relatively sensitive to base treatment and eliminate already with ammonia and amines, a more stable type was found in the 2-(4-nitrophenyl)ethyl (npe) group [2a], which is inert towards amines but will be cleaved by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a much stronger base in a clean beliminating process. The npe group has proven its advantages in a series of oligonucleotide syntheses [6], which could be extended to a unified blocking-group strategy by introduction of the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group for base protection [7] and the 2-(2,4-dinitrophenyl)ethoxycarbonyl (dnpeoc) [8], the 2-(4-nitrophenyl)ethylsulfonyl (npes) [9], and the 2-(dansylethoxycarbonyl) (dnseoc) [10] groups for sugar-OH blocking. To broaden the spectrum of b-eliminating protecting groups for oligonucleotide chemistry, the use of N-containing heteroaryl residues has been tested as activators in b-elimination reactions [11]. Since an sp 2 -hybridized ring Natom reveals a similar activation power as a NO 2 group, the pyridinyl, pyrimidinyl, and pyrazinyl moieties were chosen as new entities in these investigations.

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Arylsulfonyl chlorides in the presence of N-methylimidazole as efficient condensing reagents in phosphotriester oligonucleotide synthesis

Cited by 65 publications

References 7 publications

Nucleotide and amino acid sequences of pulmonary surfactant protein SP 18 and evidence for cooperation between SP 18 and SP 28-36 in surfactant lipid adsorption.

Nucleotide and amino acid sequences of pulmonary surfactant protein SP 18 and evidence for cooperation between SP 18 and SP 28-36 in surfactant lipid adsorption.

Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2′-hydroxyl via a phosphite triester approach

Nucleotides, Part LXVI,β-Heteroarylethyl Groups - New Phosphate-Protecting Groups for Phosphotriester Chemistry

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