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Measurement of the FMOC loading of protected amine-functionalised polymer beads

Measurement of the FMOC loading of protected amine-functionalised polymer beads
Measurement of the FMOC loading of protected amine-functionalised polymer beads
This paper presents in HPLC based procedure that has been developed for the determination of the 9-fluorenylmethoxycarbonyl (FMOC) content of protected amine-functionalised polymer beads. FMOC reagents are frequently employed both in the protection of amines and in their determination. The procedure utilises the stoichiometric base cleavage of dibenzofulvene from the protected amine using 1,8-diazabicyclo undec-7-ene. This stearically hindered base prevents the adduct formation that occurs with alternative base systems and measurement performance is enhanced by the incorporation of anthracene into the system as a non-reactive internal standard. HPLC separation of the reaction products permits the measurement of FMOC in the presence of additional chromophores that might otherwise impede direct measurement by UV-vis spectrophotometry. The procedure has been evaluated for the measurement of the FMOC content of protected amine-modified polymer beads employed in combinatorial solid phase synthesis.
fmoc protection, fmoc measurement, amine beads, combinatorial chemistry, internal standard, solid phase synthesis, hplc, dbusolid-phase synthesis, synthesis resins, chromatography, supports
0039-9140
574-577
Freeman, C.E.
de28641c-09b8-4893-9a61-69fcd76ac7d5
Howard, A.G.
12632e33-1266-49ec-ab18-8ca20c4dee72
Freeman, C.E.
de28641c-09b8-4893-9a61-69fcd76ac7d5
Howard, A.G.
12632e33-1266-49ec-ab18-8ca20c4dee72

Freeman, C.E. and Howard, A.G. (2005) Measurement of the FMOC loading of protected amine-functionalised polymer beads. Talanta, 65 (2), 574-577. (doi:10.1016/j.talanta.2004.07.021).

Record type: Article

Abstract

This paper presents in HPLC based procedure that has been developed for the determination of the 9-fluorenylmethoxycarbonyl (FMOC) content of protected amine-functionalised polymer beads. FMOC reagents are frequently employed both in the protection of amines and in their determination. The procedure utilises the stoichiometric base cleavage of dibenzofulvene from the protected amine using 1,8-diazabicyclo undec-7-ene. This stearically hindered base prevents the adduct formation that occurs with alternative base systems and measurement performance is enhanced by the incorporation of anthracene into the system as a non-reactive internal standard. HPLC separation of the reaction products permits the measurement of FMOC in the presence of additional chromophores that might otherwise impede direct measurement by UV-vis spectrophotometry. The procedure has been evaluated for the measurement of the FMOC content of protected amine-modified polymer beads employed in combinatorial solid phase synthesis.

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More information

Published date: 30 January 2005
Keywords: fmoc protection, fmoc measurement, amine beads, combinatorial chemistry, internal standard, solid phase synthesis, hplc, dbusolid-phase synthesis, synthesis resins, chromatography, supports

Identifiers

Local EPrints ID: 20795
URI: http://eprints.soton.ac.uk/id/eprint/20795
ISSN: 0039-9140
PURE UUID: a0d40452-0aa3-4429-abde-92cfaa47ad83

Catalogue record

Date deposited: 03 Mar 2006
Last modified: 06 Oct 2020 23:43

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