A new generation of reversible backbone-amide protection for the solid phase synthesis of difficult sequences
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This chapter describes backbone amide linker (BAL) strategies for the Nalpha-Fmoc solid-phase synthesis of C-terminal modified peptides. Most solid-phase protocols for the assembly of such peptides have limited generality, because they rely on the Calpha-carboxyl for attachment to the solid support. In the BAL approach, the growing peptide chain is anchored through a backbone nitrogen, thus allowing significant flexibility for chemical modification of the C-termini. In effect, any peptide containing C-terminal variations can be prepared in overall good purity and yield, with minimal side reactions, by using one or more of three variations (original and two modifications) of the BAL strategy.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Using Kobayashi's modification of the Grieco reaction, we were able to synthesize diverse 4-phenylthio-1,2,3,4-tetrahydroquinolines. These intermediates were oxidized and subsequently pyrolized to provide the corresponding quinolines. This new approach to 2-substituted quinolines was exemplified by liquid-phase production of a 25-member library. This was extended to solid-phase chemistry, starting from (l)-4-nitrophenylalanine on Wang resin, for production of a 16-member library. The latter compounds possess potentially interesting VLA-4 antagonist properties.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
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Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.
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Abstract A backbone amide linker strategy was chosen for the solid‐phase synthesis of triazole‐containing cyclic tetra‐ and pentapeptides. An alkyne‐substituted linker derived from 4‐hydroxy‐2‐methoxybenzaldehyde was elongated by using standard “Fmoc‐based” solid phase chemistry and terminated by coupling of an azido acid. In solution, the peptides were cyclized by a Cu I ‐catalyzed azide‐alkyne cycloaddition reaction. The solid‐supported synthesized linear peptides had to be cleaved prior to cyclization. As an example of cyclic tetrapeptides, a triazole analog of cyclo ‐[Pro‐Val‐Pro‐Tyr] ( 2 ) was prepared by the solid‐phase/solution‐phase method. For the cyclic pentapeptides, segetalin B ( 3 ) was chosen as a model compound to show the applicability of this method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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The use of a hydrazine derived from a backbone amide linker as a new hydrazone-based traceless linker for solid-phase organic synthesis is described. The stability of the linker was tested under various conditions, including treatment with acids, bases, and borohydrides. Final compounds can be released by selective cleavage using trimethylsilanolate. To demonstrate the versatility of the linker, the synthesis of a model compound under various reaction conditions was performed with good results.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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