Wolfgang Pfleiderer - Academia.edu (original) (raw)
Papers by Wolfgang Pfleiderer
![Research paper thumbnail of ChemInform Abstract: Synthesis of 3′-Deoxy-3′ and 5′-Deoxy-5′- [4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-triazol-1-yl]thymidine via 1,3-Dipolar Cycloaddition](https://attachments.academia-assets.com/39963121/thumbnails/1.jpg)
](Nucleosides and Nucleotides, 1997
Synthesis of new 3′-deoxy-3′ and 5′-deoxy-5′-[(4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-Triazol-... more Synthesis of new 3′-deoxy-3′ and 5′-deoxy-5′-[(4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-Triazol-1-yl]thymidine 8a-g 10a-g from 3′-azido-3′-deoxy-5′-O-monomethoxytrityl-thymidine and 5′-azido-5′deoxythymidine respectively are described. The key step is the 1,3-dipolar cycloaddition between the azido group and N-9/N-1-propargylpurine/pyrimidine derivatives.
Nucleosides and Nucleotides, 1987
Pyrazino[2,3-c]-l,2,6-thiadiazine 2,2-dioxides have been glycosylated with 1-O-acetyl derivatives... more Pyrazino[2,3-c]-l,2,6-thiadiazine 2,2-dioxides have been glycosylated with 1-O-acetyl derivatives of riboside and glucose. In deblocked N-1 glucosides a synanti rotamer equilibrium could be observed at room temperature.
Nucleosides and Nucleotides, 1997
To enhance the cellular uptake for antisense oligonucleotides or analogues a lipophilic steroid m... more To enhance the cellular uptake for antisense oligonucleotides or analogues a lipophilic steroid moiety was linked to the 5′-O- or 2′-O-position of appropriate protected thymidine or uridine simply by acid catalysed reaction with cholesterylvinylether. The corresponding cholesteryl-acetals were derivatized to the 3′-O- or 5′-O-phosphoramidites and then introduced as 5′-end terminating agents or incorporated within the sequence of oligodeoxyribonucleotides up to
Journal of the Chemical Society, Perkin Transactions 2, 1979
Nucleosides and Nucleotides, 1984
The fusion reaction between 1-trimethylsilyl-naphth[2,3-d]imidazole (3) and its 2-methyl derivati... more The fusion reaction between 1-trimethylsilyl-naphth[2,3-d]imidazole (3) and its 2-methyl derivative (4) with 2, 3, 5-tri-O-benzoyl-1-bromo-D-ribofuranose (6) leads to anomeric mixtures of the corresponding 2', 3', 5'-tri-O-benzoyl-1α- and β-D-ribofuranosylnaphth[2,3-d]imidazoles (7, 11 and 13). Separation of the anomers was achieved by chromatographical means and debenzoylation yielded the corresponding nucleosides (8, 12 and 10, 14). Structural proofs are based on elementary analysis, UV-
ChemInform, 1996
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Nucleosides and Nucleotides, 1986
Fusion of 1-trimethylsilylnaphtho[2,3-d]-1,2,3-triazole (4) and 2,3,5-tri-0-benzoyl-1-bromo-D-rib... more Fusion of 1-trimethylsilylnaphtho[2,3-d]-1,2,3-triazole (4) and 2,3,5-tri-0-benzoyl-1-bromo-D-ribofuranose (5) in presence of KI leads at 130C to an anomeric mixture of the corresponding 1-(2,3,5-tri-O-benzoyl-α- and -β-D-ribofuranosyl)-naphtho-[2,3-d]-1,2,3-triazoles (6 and 8). Separation of the anomers was achieved by chromatographical means. Debenzoylation led to the free nucleosides 7 and 9 respectively. Structural proofs are based on elementary analyses, UV- and H-NMR-spectra.
Nucleosides and Nucleotides, 1987
... Chem. 261, 6836-6839. 10. Haugh, MC , Cayley, PT , Serafinowska, HT , Norman, DG , Reese, CB,... more ... Chem. 261, 6836-6839. 10. Haugh, MC , Cayley, PT , Serafinowska, HT , Norman, DG , Reese, CB,#& Kerr, IM (1983) &. 2. Biochem. 132, 77-84. 11. Kariko, K., Li, SW, Sobol, R. W., Jr., Reichenbach, NL, Charu-bala, R., Pfleiderer, W., & Suhadolnik, RJ, manuscript submitted.
Nucleosides and Nucleotides, 1987
Enzymatically and chemically synthesized 2–5A phosphorothioates stereochemical altered in the 2′,... more Enzymatically and chemically synthesized 2–5A phosphorothioates stereochemical altered in the 2′,5′-internucleotide linkages gave a series of metabolically stable chiral 2–5A derivatives that have been used to study the stereochemical requirements for binding to and activation of RNase L. The RpRp and SpRp, but not the RpSp or SpSp, trimer core isomers could bind to and activate RNase L
Nucleosides and Nucleotides, 1997
New 2′,5′-oligonucleotide trimers containing 2′,3′-dideoxy-3′-fluoro derivatives of adenosine at ... more New 2′,5′-oligonucleotide trimers containing 2′,3′-dideoxy-3′-fluoro derivatives of adenosine at the 2′-terminal end of oligomers have been synthesized. Some of the synthesized trimers showed biological inhibitions of HIV-1 reverse transcriptase and HIV-1 induced syncytia formation.
Biochemistry, Jan 3, 1987
The chiral and achiral phosphorothioate analogues of 2',5'-oligoadenylates (2-5A) have be... more The chiral and achiral phosphorothioate analogues of 2',5'-oligoadenylates (2-5A) have been enzymatically synthesized from the Sp and Rp isomers of adenosine 5'-O-(2-thiotriphosphate) [(Sp)-ATP beta S and (Rp)-ATP beta S, respectively] and adenosine 5'-O-(3-thiotriphosphate) (ATP gamma S) by 2-5A synthetase from L929 cells and lysed rabbit reticulocytes. These 2',5'-phosphorothioate analogues were separated, purified, and structurally characterized. While ATP gamma S and (Sp)-ATP beta S were as efficient substrates for the 2-5A synthetase as was ATP, (Rp)-ATP beta S was more than 50-fold less efficient a substrate. The beta- and gamma-phosphorothioates were more resistant to enzymatic hydrolysis than was authentic 2-5A. Compared to 2-5A, there were marked differences in the biological activities of the 2',5'-phosphorothioates as determined by (i) binding to 2-5A-dependent endoribonuclease (RNase L), (ii) activation of RNase L to hydrolyze RNA, and (ii...
ChemInform, 1991
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Nucleosides and Nucleotides, 1999
Some new 2',5'-oligonucleotide trimers containing 5'-terminal 5'-... more Some new 2',5'-oligonucleotide trimers containing 5'-terminal 5'-amino-5'-deoxy- and 5'-amino-3',5'-dideoxyadenosine derivatives have been synthesized. Some of the trimers showed biological inhibitions of HIV-1 reverse transcriptase (RT), HIV-1 induced syncytia formation and PCR amplification.
Nucleosides and Nucleotides, 1997
Synthesis of new 3′-deoxy-3′ and 5′-deoxy-5′-[(4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-Triazol-... more Synthesis of new 3′-deoxy-3′ and 5′-deoxy-5′-[(4-(purin-9-yl/pyrimidin-1-yl)methyl-1,2,3-Triazol-1-yl]thymidine 8a-g 10a-g from 3′-azido-3′-deoxy-5′-O-monomethoxytrityl-thymidine and 5′-azido-5′deoxythymidine respectively are described. The key step is the 1,3-dipolar cycloaddition between the azido group and N-9/N-1-propargylpurine/pyrimidine derivatives.
Nucleosides and Nucleotides, 1987
Pyrazino[2,3-c]-l,2,6-thiadiazine 2,2-dioxides have been glycosylated with 1-O-acetyl derivatives... more Pyrazino[2,3-c]-l,2,6-thiadiazine 2,2-dioxides have been glycosylated with 1-O-acetyl derivatives of riboside and glucose. In deblocked N-1 glucosides a synanti rotamer equilibrium could be observed at room temperature.
Nucleosides and Nucleotides, 1997
To enhance the cellular uptake for antisense oligonucleotides or analogues a lipophilic steroid m... more To enhance the cellular uptake for antisense oligonucleotides or analogues a lipophilic steroid moiety was linked to the 5′-O- or 2′-O-position of appropriate protected thymidine or uridine simply by acid catalysed reaction with cholesterylvinylether. The corresponding cholesteryl-acetals were derivatized to the 3′-O- or 5′-O-phosphoramidites and then introduced as 5′-end terminating agents or incorporated within the sequence of oligodeoxyribonucleotides up to
Journal of the Chemical Society, Perkin Transactions 2, 1979
Nucleosides and Nucleotides, 1984
The fusion reaction between 1-trimethylsilyl-naphth[2,3-d]imidazole (3) and its 2-methyl derivati... more The fusion reaction between 1-trimethylsilyl-naphth[2,3-d]imidazole (3) and its 2-methyl derivative (4) with 2, 3, 5-tri-O-benzoyl-1-bromo-D-ribofuranose (6) leads to anomeric mixtures of the corresponding 2', 3', 5'-tri-O-benzoyl-1α- and β-D-ribofuranosylnaphth[2,3-d]imidazoles (7, 11 and 13). Separation of the anomers was achieved by chromatographical means and debenzoylation yielded the corresponding nucleosides (8, 12 and 10, 14). Structural proofs are based on elementary analysis, UV-
ChemInform, 1996
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Nucleosides and Nucleotides, 1986
Fusion of 1-trimethylsilylnaphtho[2,3-d]-1,2,3-triazole (4) and 2,3,5-tri-0-benzoyl-1-bromo-D-rib... more Fusion of 1-trimethylsilylnaphtho[2,3-d]-1,2,3-triazole (4) and 2,3,5-tri-0-benzoyl-1-bromo-D-ribofuranose (5) in presence of KI leads at 130C to an anomeric mixture of the corresponding 1-(2,3,5-tri-O-benzoyl-α- and -β-D-ribofuranosyl)-naphtho-[2,3-d]-1,2,3-triazoles (6 and 8). Separation of the anomers was achieved by chromatographical means. Debenzoylation led to the free nucleosides 7 and 9 respectively. Structural proofs are based on elementary analyses, UV- and H-NMR-spectra.
Nucleosides and Nucleotides, 1987
... Chem. 261, 6836-6839. 10. Haugh, MC , Cayley, PT , Serafinowska, HT , Norman, DG , Reese, CB,... more ... Chem. 261, 6836-6839. 10. Haugh, MC , Cayley, PT , Serafinowska, HT , Norman, DG , Reese, CB,#& Kerr, IM (1983) &. 2. Biochem. 132, 77-84. 11. Kariko, K., Li, SW, Sobol, R. W., Jr., Reichenbach, NL, Charu-bala, R., Pfleiderer, W., & Suhadolnik, RJ, manuscript submitted.
Nucleosides and Nucleotides, 1987
Enzymatically and chemically synthesized 2–5A phosphorothioates stereochemical altered in the 2′,... more Enzymatically and chemically synthesized 2–5A phosphorothioates stereochemical altered in the 2′,5′-internucleotide linkages gave a series of metabolically stable chiral 2–5A derivatives that have been used to study the stereochemical requirements for binding to and activation of RNase L. The RpRp and SpRp, but not the RpSp or SpSp, trimer core isomers could bind to and activate RNase L
Nucleosides and Nucleotides, 1997
New 2′,5′-oligonucleotide trimers containing 2′,3′-dideoxy-3′-fluoro derivatives of adenosine at ... more New 2′,5′-oligonucleotide trimers containing 2′,3′-dideoxy-3′-fluoro derivatives of adenosine at the 2′-terminal end of oligomers have been synthesized. Some of the synthesized trimers showed biological inhibitions of HIV-1 reverse transcriptase and HIV-1 induced syncytia formation.
Biochemistry, Jan 3, 1987
The chiral and achiral phosphorothioate analogues of 2',5'-oligoadenylates (2-5A) have be... more The chiral and achiral phosphorothioate analogues of 2',5'-oligoadenylates (2-5A) have been enzymatically synthesized from the Sp and Rp isomers of adenosine 5'-O-(2-thiotriphosphate) [(Sp)-ATP beta S and (Rp)-ATP beta S, respectively] and adenosine 5'-O-(3-thiotriphosphate) (ATP gamma S) by 2-5A synthetase from L929 cells and lysed rabbit reticulocytes. These 2',5'-phosphorothioate analogues were separated, purified, and structurally characterized. While ATP gamma S and (Sp)-ATP beta S were as efficient substrates for the 2-5A synthetase as was ATP, (Rp)-ATP beta S was more than 50-fold less efficient a substrate. The beta- and gamma-phosphorothioates were more resistant to enzymatic hydrolysis than was authentic 2-5A. Compared to 2-5A, there were marked differences in the biological activities of the 2',5'-phosphorothioates as determined by (i) binding to 2-5A-dependent endoribonuclease (RNase L), (ii) activation of RNase L to hydrolyze RNA, and (ii...
ChemInform, 1991
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Nucleosides and Nucleotides, 1999
Some new 2',5'-oligonucleotide trimers containing 5'-terminal 5'-... more Some new 2',5'-oligonucleotide trimers containing 5'-terminal 5'-amino-5'-deoxy- and 5'-amino-3',5'-dideoxyadenosine derivatives have been synthesized. Some of the trimers showed biological inhibitions of HIV-1 reverse transcriptase (RT), HIV-1 induced syncytia formation and PCR amplification.