Tagging strategy

Tetteh, K.K.A., Loukas, A., Tripp, C. and Maizels, R.M. (1999) Identification of abundantly-expressed novel and conserved genes from infective stage larvae of Toxocara canis by an expressed sequence tag strategy. Infection and Immunity 67, 4771-4779. 

Leitner, A., and Lindner, W. (2004) Current chemical tagging strategies for proteome analysis by mass spectrometry./. Chrom. B813, 1-26. 

Zappacosta, F., and Annan, R.S. (2004) N-terminal isotope tagging strategy for quantitative proteomics Results-driven analysis of protein abundance changes. Anal. Chem. 76, 6618-6627. 

The described fluorous-tag strategy has also been applied to the synthesis of biaryl-substituted hydantoins (Scheme 7.81) [94]. 4-Hydroxybenzaldehyde was converted into the corresponding perfluorinated species, which was then subjected to a reductive amination. The resulting amine was treated with an isocyanate to produce the fluorous-tagged urea, which spontaneously cyclized to form the corresponding hydantoin. Finally, the fluorous tag was detached by a Suzuki-type carbon-carbon bond formation to furnish the desired target structure in good yield. 

Selective loop cleavage via intermediate y-lactone formation using methanesulfonic acid in MeOH liberates the N-terminus without concomitant cleavage of the peptide chain and allows determination of the sequence of the peptide without tagging strategies. 

In this technique, an rf encodable microchip is coupled with a capsule of derivatized polystyrene resin such that each unique synthesis site can be tagged with a unique identifier code. The inert nature of the rf transponder construction renders this tagging strategy compatible with virtually all synthetic methods. Additionally, the noninvasive transmission or retrieval of information from any capsule is unambiguous and instantaneous, avoiding the possibility of long reaction and/or analysis times associated with chemical tags. 

Z. Luo, Q. Zhang, Y. Oderaotoshi, and D. P. Curran, Fluorous mixture synthesis A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds, Science, 291 (2001), 1766-1769. 

Fluorous chemistry integrates the characteristics of solution-phase reactions and the phase tag strategy developed for solid-phase chemistry [7-15], Perfluoroalkyl chains instead of polymer beads are used as the phase tags to facilitate the separation process. In 2001 the Curran group first reported the concept of fluorous mixture synthesis (FMS) for solution-phase library synthesis [16], FMS is able to produce individual pure compounds without the effort of deconvolution. It adapts literature procedures to synthesize complex natural products, their enantiomers and diastereomers. FMS can also be used for the development of new synthetic protocols and to make novel drug-like molecules [17, 18],... 

The synthetic scope for making murisolin stereoisomers has been extended through the development of the first double tagging strategy [34, 35] A mixture of four stereoisomers of dihydroxytetrahydofuran encoded with four fluorous tags at C-19 and C-20 was... 

Zhang, W. (2004) Fluorous tagging strategy for solution-phase synthesis of small molecules, peptides and oligosaccharides. Curr. Opin. Drug Discov. Develop., 7, 784—797. 

Zhang, Q. S., Rivkin, A. and Curran, D. P. (2002) Quasiracemic synthesis concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine. J. Am. Chem. Soc., 124, 5774—5781. 

Manku, S. and Curran, D. P. (2005) Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates../. Org. Chem., 70, 4470-4473. 

Smith, R.D., Anderson, G.A., Lipton, M.S., Pasa-Tolic, L., Shen, Y., Conrads, T.P., Veenstra, T.D., and Udseth, H.R. 2002. An accurate mass tag strategy for quantitative and high-throughput measurements. Proteomics 2, 513-523. 

We now discuss applications of the ionic tagging strategy to the design of catalysts for the direct asymmetric Michael addition of carbonyl compounds to nitroalkenes. Table 1.3 shows a few examples. 

A more elaborate molecular design is at the basis of a solvent-less reaction protocol. The ionic-tagging strategy, combined with the installation of a... 

---