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1.
J Comb Chem ; 9(6): 1012-27, 2007.
Article in English | MEDLINE | ID: mdl-17900168

ABSTRACT

Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins for Polymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH2, were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins. Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR. These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and at much higher loading levels than standard amphiphilic resins of similar solvent compatibility.


Subject(s)
Enkephalin, Leucine/chemical synthesis , Ethers/chemistry , Neurotransmitter Agents/chemical synthesis , Polyethylene Glycols/chemistry , Resins, Synthetic/chemical synthesis , Alkenes/chemistry , Hydroxylation , Magnetic Resonance Spectroscopy , Models, Chemical , Osmium Tetroxide/chemistry , Oximes/chemistry , Polymethyl Methacrylate/chemistry , Solvents/chemistry
2.
Nat Mater ; 5(10): 787-90, 2006 Oct.
Article in English | MEDLINE | ID: mdl-16951674

ABSTRACT

Since the introduction of molecular computation, experimental molecular computational elements have grown to encompass small-scale integration, arithmetic and games, among others. However, the need for a practical application has been pressing. Here we present molecular computational identification (MCID), a demonstration that molecular logic and computation can be applied to a widely relevant issue. Examples of populations that need encoding in the microscopic world are cells in diagnostics or beads in combinatorial chemistry (tags). Taking advantage of the small size (about 1 nm) and large 'on/off' output ratios of molecular logic gates and using the great variety of logic types, input chemical combinations, switching thresholds and even gate arrays in addition to colours, we produce unique identifiers for members of populations of small polymer beads (about 100 microm) used for synthesis of combinatorial libraries. Many millions of distinguishable tags become available. This method should be extensible to far smaller objects, with the only requirement being a 'wash and watch' protocol. Our focus on converting molecular science into technology concerning analog sensors, turns to digital logic devices in the present work.

3.
Beilstein J Org Chem ; 2: 15, 2006 Aug 25.
Article in English | MEDLINE | ID: mdl-16934142

ABSTRACT

Aromatic aldehydes and ketones as well as aromatic epoxides are selectively reduced to the corresponding alcohols under mild conditions using conventional hydrogen in the presence of Pd(0)EnCat 30NP catalyst. The reactions were performed at room temperature during 16 hours with high to excellent conversions of the corresponding products.

4.
Org Lett ; 5(24): 4665-8, 2003 Nov 27.
Article in English | MEDLINE | ID: mdl-14627410

ABSTRACT

[reaction: see text] Pd nanoparticles (approximately 2 nm in size) microencapsulated in polyurea is an efficient and recyclable catalyst for reductive ring-opening hydrogenolysis of epoxides, using either HCOOH/Et(3)N or H(2) as a hydrogen donor.

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