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Angewandte Chemie International Edition 02/2006; 45(4):548-51. · 13.45 Impact Factor
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ABSTRACT: [reaction: see text] Significant rate acceleration of metal-catalyzed Michael addition reactions in water was observed upon addition of small, dibasic ligands. Ytterbium triflate and TMEDA was the most effective combination leading to a nearly 20-fold faster reaction than in the absence of ligand.
The Journal of Organic Chemistry 02/2006; 71(1):352-5. · 4.45 Impact Factor
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Angewandte Chemie 12/2005; 118(4):562 - 565.
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ABSTRACT: An extremely efficient asymmetric synthesis of a pyrrolidine azasugar was completed in only four steps in water, without the use of protecting groups and in 60% overall yield from a simple, achiral bis-electrophile.
Chemical Communications 05/2005; · 6.17 Impact Factor
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ABSTRACT: A general problem that exists in the assembly of large and organized DNA structures from smaller fragments is secondary structure that blocks or prevents it. For example, it is common to assemble longer synthetic DNA and RNA fragments by ligation of smaller synthesized units, but blocking secondary structure can prevent the formation of the intended complex before enzymatic ligation can occur. In addition, there is a general need for protecting groups that would block reactivity of some DNA bases in a sequence, leaving others free to react or hybridize. Here we describe such a strategy. The approach involves the protecting group dimethylacetamidine (Dma), which we show to remain intact on exocyclic amines of adenine bases while other bases carrying commercially available 'ultra mild deprotection' protecting groups are removed by potassium carbonate in methanol. The intact Dma groups prevent unwanted hybridization at undesired sites, thus encouraging it to occur where intended, and allowing for successful ligations. The Dma group is then deprotected by treatment with ammonia in methanol. Other common amine protecting groups such as benzoyl and allyloxycarbonyl were not successful in such a strategy, at least in part because they did not prevent hybridization. We demonstrate the method in the synthesis of a circular 54mer oligonucleotide composed of nine human telomere repeats, which was not possible to assemble by conventional methods.
Nucleic Acids Research 11/2002; 30(19):e101. · 8.03 Impact Factor
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Ulf M Lindström
Chemical Reviews 09/2002; 102(8):2751-72. · 40.20 Impact Factor