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A new bio-compatible pH cleavable linker for solid-phase synthesis of a squalamine analogue

Chitkul, B., Atrash, B. and Bradley, M. (2001) A new bio-compatible pH cleavable linker for solid-phase synthesis of a squalamine analogue Tetrahedron Letters, 42, (35), pp. 6211-6214. (doi:10.1016/S0040-4039(01)01217-5).

Record type: Article


Linkers that can be cleaved directly within the biological assay offer some advantages over traditional linkers in the range of direct screening applications that the associated libraries can be utilised for. The 1,6-elimination process is an efficient method of cleaning compounds from substituted 4-hydroxymethyl phenols, although giving rise to quinone methide by-products. Here, we report on a linker that uses an in-built amine 'activator' to cleave a phenoxy ester and hence to activate the linker to 1,6-elimination. An analogue of the antibacterial agent squalamine was synthesised and released using this linker strategy.

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Published date: 27 August 2001
Keywords: solid-phase, synthesis, linker, squalamine protected peptide-fragments, organic-synthesis, combinatorialchemistry, resin, libraries


Local EPrints ID: 19449
ISSN: 0040-4039
PURE UUID: 00986b2c-bbe1-407f-b06c-688f96d2d9b2

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Date deposited: 14 Feb 2006
Last modified: 17 Jul 2017 16:31

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Author: B. Chitkul
Author: B. Atrash
Author: M. Bradley

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