Automation of Fluorous Solid-phase Extraction for Parallel Synthesis

Overview

Journal J Comb Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2006 Nov 14

PMID 17096578

Citations 4

Authors

Wei Zhang

Yimin Lu

Affiliations

Soon will be listed here.

Abstract

An automatic fluorous solid-phase extraction (F-SPE) technique is developed by using FluoroFlash SPE cartridges on the RapidTrace workstation. A 10-module workstation has the capability to complete a maximum of 100 SPEs each round in 1-2 h. Another important feature of the RapidTrace system is that it has the capability to load slurry samples onto the F-SPE cartridges. The F-SPE cartridge charged with 2 g of fluorous silica gel is used to purify up to 200 mg of crude sample. Sample loading, elution solvent, cartridge reuse, and SPE reproducibility are evaluated. The automatic SPE system is used for purification of a small urea library generated from amine-scavenging reactions using fluorous dichlorotriazine, a 96-membered amide library generated using 2-chloro-4,6-bis[(perfluorohexyl)propyloxy]-1,3,5-triazine as the coupling agent, and another 96-membered library generated from fluorous Mitsunobu reactions. Approximately 90% of the products have > 90% purity after F-SPE.

Citing Articles

The azido acid approach to beta-peptides: parallel synthesis of a tri-beta-peptide library by fluorous tagging.

Wang X, Nelson S, Curran D Tetrahedron. 2009; 63(27):6141-6145.

PMID: 19562094 PMC: 2701693. DOI: 10.1016/j.tet.2007.03.034.

Fluorous-based small-molecule microarrays for the discovery of histone deacetylase inhibitors.

Vegas A, Bradner J, Tang W, McPherson O, Greenberg E, Koehler A Angew Chem Int Ed Engl. 2007; 46(42):7960-4.

PMID: 17868168 PMC: 2790065. DOI: 10.1002/anie.200703198.

Fluorous synthesis of sclerotigenin-type benzodiazepine-quinazolinones.

Zhang W, Williams J, Lu Y, Nagashima T, Chu Q Tetrahedron Lett. 2007; 48(4):563-565.

PMID: 17479166 PMC: 1865100. DOI: 10.1016/j.tetlet.2006.11.127.

Fluorous-enhanced multicomponent reactions for making drug-like library scaffolds.

Zhang W Comb Chem High Throughput Screen. 2007; 10(3):219-29.

PMID: 17346120 PMC: 1857346. DOI: 10.2174/138620707780126697.

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