Selectivity of montmorillonite catalyzed prebiotic reactions of D, L-nucleotides (2007)
Pitsch, Stefan, Ferris, James P.
The montmorillonite-catalyzed reactions of the 5′-phosphorimidazolides of D, L-adenosine (D, L-ImpA) (Figure 1a. N = A, R = H) and D, L-uridine (Figure 1a., N = U, R = H) yields oligomers that were...
Molecular basis of RNA recognition by the human alternative splicing factor Fox-1 (2006)
Auweter, Sigrid D., Fasan, Rudi, Reymond, Luc, Underwood, Jason G., Black, Douglas L., Pitsch, Stefan, ...
The Fox-1 protein regulates alternative splicing of tissue-specific exons by binding to GCAUG elements. Here, we report the soln. structure of the Fox-1 RNA binding domain (RBD) in complex with...
Kinetics of RNA Refolding in Dynamic Equilibrium by 1H-Detected 15N Exchange NMR Spectroscopy (2006)
Wenter, Philipp, Bodenhausen, Geoffrey, Dittmer, Jens, Pitsch, Stefan
By implementing new NMR methods that were designed to map very slow exchange processes we have investigated and characterized the refolding kinetics of a thermodynamically stable 34mer RNA sequence...
Wenter, Philipp, Reymond, Luc, Auweter, Sigrid D., Allain, Frédéric H.-T., Pitsch, Stefan
We report an optimized synthesis of all canonical 2'-O-TOM protected ribonucleoside phosphoramidites and solid supports containing [13C5]-labeled ribose moieties, their sequence-specific introduction...
Wenter, Philipp, Reymond, Luc, Auweter, Sigrid D., Allain, Frédéric H.-T., Pitsch, Stefan
We report an optimized synthesis of all canonical 2′-O-TOM protected ribonucleoside phosphoramidites and solid supports containing [13C5]-labeled ribose moieties, their sequence-specific...
Hoelzl, Georg, Oberacher, Herbert, Pitsch, Stefan, Stutz, Alfred, Huber, Christian G.
Ion-pair reversed-phase high-performance liq. chromatog. (IP-RP-HPLC) has been evaluated as a method for the fractionation and desalting of ribonucleic acids prior to their characterization by...
Structure of PTB Bound to RNA: Specific Binding and Implications for Splicing Regulation (2005)
Oberstrass, Florian C., Auweter, Sigrid D., Erat, Michele, Hargous, Yann, Henning, Anke, Wenter, Philipp, ...
The polypyrimidine tract binding protein (PTB) is a 58-kDa RNA binding protein involved in multiple aspects of mRNA metab., including the repression of alternative exons. We have detd. the soln....
Preparation of modified RNA sequences for biological research (2005)
Pitsch, Stefan, Ackermann, Damian, Denarie, Cyrille, Meylan, Frederic, Meyyappan, Muthulaniappan, Muller, Evelyne, ...
Our group is working on the development of reliable access to biol. relevant, long, and modified RNA sequences. Here, we briefly present the chem. synthesis of such sequences with...
Spontaneous aminoacylation of a RNA sequence containing a 3'-terminal 2'-thio-adenosine (2005)
Porcher, Sebastien, Meyyappan, Muthuppalaniappan, Pitsch, Stefan
We report the synthesis of a modified 8-mer RNA sequence, (C-C-C-C-A-C-C-(2'-thio)A)-RNA 5'-(dihydrogen phosphate) contg. a 3'-terminal 2'-thio-adenosine and its spontaneous and site-specific...
Porcher, Sebastien, Pitsch, Stefan
The first results of a study aiming at an efficient prepn. of a large variety of 2'-O-[(triisopropylsilyl)oxy]methyl(=tom)-protected ribonucleoside phosphoramidite building blocks contg. modified...
Kinetics of photoinduced RNA refolding by real-time NMR spectroscopy (2005)
Wenter, Philipp, Fuertig, Boris, Hainard, Alexandre, Schwalbe, Harald, Pitsch, Stefan
By introducing a photolabile group in the Watson-Crick base-pairing site of a guanosine residue, a bistable 20-base RNA sequence was forced into a less stable conformation. A single laser pulse...
On facts and artefacts: The difficulty to evaluate an artificial nuclease (2003)
Pitsch, Stefan, Scheffer, Ute, Hey, Markus, Strick, Andreas, Goebel, Michael W.
A no. of promising synthetic catalysts for the hydrolytic degrdn. of RNA have been developed in recent years. Some of them show remarkable selectivity for pyrimidine nucleotides. The general problem...
Pitsch, Stefan, Wendeborn, Sebastian, Krishnamurthy, Ramanarayanan, Holzner, Armin, Minton, Mark, Bolli, Martin, ...
Pyranosyl-RNA (\"p-RNA\") is an oligonucleotide system isomeric to natural RNA and composed of the very same building blocks as RNA. Its generational, chem., and informational properties are deemed...
Wenter, Philipp, Pitsch, Stefan
We present optimized reaction conditions for the conversion of 2'-O-{[(triisopropylsilyl)oxy]methyl}(tom) protected uridine and adenosine nucleosides into the corresponding protected (3-15N)-labeled...
Ackermann, Damian, Pitsch, Stefan
The prepn. and the pairing properties of the new 3'-deoxyribopyranose (4'->2')-oligonucleotide (= p-DNA) pairing system, based on 3'-deoxy-b-D-ribo-pyranose nucleosides is presented. D-Xylose was...
Ackermann, Damian, Wu, Xiaolin, Pitsch, Stefan
By automated synthesis, we prepd. hybrid oligonucleotides consisting of covalently linked RNA and p-DNA sequences (p-DNA = 3'-deoxyribopyranose (4'->2')-oligonucleotides). The pairing properties of...
Bicyclo[3.2.1]amide-DNA: a chiral, nonchiroselective base-pairing system (2002)
Ahn, Dae-Ro, Egger, Anita, Lehmann, Christian, Pitsch, Stefan, Leumann, Christian J.
The design, synthesis, and base-pairing properties of bicyclo[3.2.1]amide-DNA (bca-DNA), a novel phosphodiester-based DNA analog, are reported. This analog consists of a conformationally constrained...
Ebert, Marc-Olivier, Ackermann, Damian, Pitsch, Stefan, Jaun, Bernhard
The detn. of the soln. structure of small non-natural oligopeptides and oligonucleotides by NMR, which is one of the main research topics of our group, is illustrated on the example of an 8-mer p-DNA...
Protecting groups for the synthesis of ribonucleic acids (2001)
A review, with 17 refs. Methods for the regioselective introduction of alkoxymethyl-groups into the 2'-O-position of 5'-O-dimethoxytritylated, nucleobase-protected ribonucleosides and for the...
Towards a total synthesis of aminoacylated t-RNAs (2001)
In the ribosomal biosynthesis of proteins, the aminoacylated t-RNAs serve as carriers of the amino acids. A total synthesis of these biol. key-compds. would allow the site-specific incorporation of...
Pitsch, Stefan, Weiss, Patrick A., Jenny, Luzi, Stutz, Alfred, Wu, Xiaolin
A method for the introduction of the 2'-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5'-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2'-O-tom-protected...
Synthesis of Pyrrolidinone PNA: A Novel Conformationally Restricted PNA Analogue (2001)
Puschl, Ask, Boesen, Thomas, Zuccarello, Guido, Dahl, Otto, Pitsch, Stefan, Nielsen, Peter E.
To preorganize PNA for duplex formation, a new cyclic pyrrolidinone PNA analog has been designed. In this analog the aminoethyl-glycine backbone and the methylene-carbonyl linker are connected,...
Joshi, Prakash C., Ferris, James P., Pitsch, Stefan
The reaction of d,l-5'-activated nucleotide of adenosine in the presence and absence of montmorillonite gave 60:40 and 96:4 ratios, resp. of the d,d- and l,l:d,l- and l,d-dimers. [on SciFinder (R)]
Pitsch, Stefan, Krishnamurthy, Ramanarayanan, Arrhenius, Gustaf
Environmental conditions play an important role in conceptual studies of prebiotically relevant chem. reactions that could have led to functional biomols. The necessary source compds. are likely to...
Rajwanshi, Vivek K., Hakansson, Anders E., Sorensen, Mads D., Pitsch, Stefan, Singh, Sanjay K., Kumar, Ravindra, ...
The authors evaluated the RNA binding of all eight possible stereoisomers of LNA. Synthesis of \"a-l-xylo-LNA\" has been accomplished and the remaining four stereoisomers, all enantiomers of the four...
Stutz, Alfred, Hobartner, Claudia, Pitsch, Stefan
With the aim to develop a general approach to a total synthesis of amino-acylated t-RNAs and analogs, we describe the synthesis of stabilized, amino-acylated RNA fragments, which, upon ligation,...
Specialists for RNA synthesis (2000)
Weiss, Patrick A., Pitsch, Stefan
In contrast to DNA-related research, RNA-related research is limited by the availability of synthetic sequences. Recent improvements in chem. synthesis allow Xeragon AG to offer custom RNA sequences...
The prepn. of building blocks for the incorporation of 6'-O-(5-bromopentyl)-substituted b-D-allofuranosylnucleosides and 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleosides into oligonucleotide...
Agent-driven online business in virtual communities (2000)
Arndt Kraft, Stefan Pitsch, Michael Vetter
As Virtual Communities and electronic commerce are merging into each other, following the users wants and companies needs, at the same time electronic commerce is starting to support the whole buying...
Kozlov, Igor A., Politis, Panagiotis K., Pitsch, Stefan, Herdewijn, Piet, Orgel, Leslie E.
The authors compare the enantiomeric cross-inhibition of D- and L-guanosine 5'-phosphoro-2-methyl-imidazole (I) polymn. on C10 (RNA), dC10 (DNA), or hC10 (hexitol nucleic acid) (II). RNA or DNA...
Micura, Ronald, Kudick, Rene, Pitsch, Stefan, Eschenmoser, Albert
A comparison of relevant properties of selected pyranosyl-RNA and homo-DNA duplexes offers an opportunity for testing the thesis of the predominant role of inter-strand base stacking in...
Synthesis of some D-ribose phosphates (1999)
Pitsch, Stefan, Spinner, Christoph, Atsumi, Kunio, Ermert, Philip
Unambitious syntheses of D-ribose 2-phosphate, 3-phosphate, 4-phosphate, 2,3-diphosphate, 3,4-diphosphate, 2,4-diphosphate, cyclic 2,3-phosphate, cyclic 3,4-phosphate, and cyclic 2,4-phosphate are...
Pitsch, Stefan, Weiss, Patrick A., Wu, Xiaolin, Ackermann, Damian, Honegger, Thomas
Two sets of RNA phosphoramidites, carrying the (fluoride-labile) 2'-O-[(triisopropylsilyl)oxy]methyl (tom) group and the (photolabile) [(R)-1-(2-nitrophenyl)ethoxy]methyl ((R)-npeom) group, were...
Automated RNA-synthesis with photocleavable sugar and nucleobase protecting groups (1999)
A synthetic method for the N-alkyloxycarbonylation of adenine and guanine nucleosides was developed and used for the prepn. of RNA-phosphoramidites carrying photolabile sugar and nucleobase...
Functionalization of the Sugar Moiety of Oligoribonucleotides on Solid Support (1999)
A solid-phase method for the introduction of a variety of different side chains into oligoribonucleotides is presented. It is based on a b-D-allofuranosyl phosphoramidite with a...
Kozlov, Igor A., Pitsch, Stefan, Orgel, Leslie E.
The oligomerization of activated D- and L- and racemic guanosine-5'-phosphoro-2-methylimidazole on short templates contg. D- and L-deoxycytidylate has been studied. Results obtained with D-oligo(dC)s...
A method for the facile prepn. of oligoribonucleotide analogs contg. b-D-allo-furanosyl nucleosides with addnl. functional groups tethered to the 6'-O positions is presented. It is based on the...
Pyranosyl-RNA. Further observations on replication. Part 5 (1997)
Bolli, Martin, Micura, Ronald, Pitsch, Stefan, Eschenmoser, Albert
Replication (single-turnover) of pyranosyl-RNA (p-RNA) sequences can be accomplished reliably by template-directed ligation of 2',3'-cyclophosphates of short oligomers. The ligation process was...
An efficient synthesis of enantiomeric ribonucleic acids from D-glucose (1997)
Enantiomeric oligoribonucleotides (ent-RNA) up to a sequence length of 35, consisting of the (L-configurated) nucleosides ent-adenosine, ent-guanosine, ent-cytidine, ent-uridine, and...
Towards the synthesis of functionalized ribonucleic acids (1997)
A brief review with 5 refs. on the author's work. [on SciFinder (R)]
Krishnamurthy, Ramanarayanan, Pitsch, Stefan, Minton, Mark, Miculka, Christian, Windhab, Norbert, Eschenmoser, Albert
The authors report here pyranosyl-RNA: base pairing between homochiral oligonucleotide strands of opposite sense of chirality. [on SciFinder (R)]
Schloenvogt, Irene, Pitsch, Stefan, Lesueur, Catherine, Eschenmoser, Albert, Jaun, Bernhard
The soln. structure of the duplex formed by self-pairing of the p-RNA octamer b-D-ribopyranosyl-(2'->4')-(CGAATTCG) was studied by NMR techniques and, independently, by mol.-dynamics calcns. The...
Pyranosyl-RNA ('p-RNA'): base-pairing selectivity and potential to replicate (1995)
Pitsch, Stefan, Krishnamurthy, Ramanarayanan, Bolli, Martin, Wendeborn, Sebastian, Holzner, Armin, Minton, Mark, ...
A review and discussion, with 42 refs. Base pairing in p-RNA (b-D-ribopyranosyl-(4'->2')-oligonucleotides) is not only stronger than in DNA and RNA, but also more selective in the sense that it is...
Pitsch, Stefan, Pombo-Villar, Esteban, Eschenmoser, Albert
Oxiranecarbonitrile in basic aq. soln. at room temp. reacts regioselectively with inorg. phosphate to give the cyanohydrin of 2-oxoethyl phosphate ('glycolaldehyde phosphate'), a source of (the...
Why pentose- and not hexose-nucleic acids? Part VII. Pyranosyl-RNA('p-RNA') (1993)
Pitsch, Stefan, Wendeborn, Sebastian, Jaun, Bernhard, Eschenmoser, Albert
A review with 39 refs. Qual. conformational anal. of the entirety of conceivable hexo- and pentopyranosyl oligonucleotide systems derived from the diastereoisomeric aldohexoses (CH2O)6 and...
Diss. Nr. 10055 Naturwiss. ETH Zürich.
Mueller, Daniel, Pitsch, Stefan, Kittaka, Atsushi, Wagner, Ernst, Wintner, Claude E., Eschenmoser, Albert
Glycoaldehyde phosphate aldomerizes in aq. NaOH to a product mixt. contg. the racemates of two diastereomeric tetrose 2,4-diphosphates and 8 hexose 2,4,5-triphosphates. The aldomerization of...
Müller, Daniel, Pitsch, Stefan, Kittaka, Atsushi, Wagner, Ernst, Wintner, Claude E., Eschenmoser, Albert
Dresden, Pädag. Hochsch., Diss., 1982 (Nicht f.d. Austausch).