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Synthesis 2009(20): 3460-3466  
DOI: 10.1055/s-0029-1216952
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of an Arginine Tagged [Cys155-Arg180] Fragment of NY-ESO-1: Elimination of an Undesired By-product Using ‘In House’ Resins

Paul W. R. Harris*, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: paul.harris@auckland.ac.nz; e-Mail: m.brimble@auckland.ac.nz;
Further Information

Publication History

Received 5 June 2009
Publication Date:
21 August 2009 (online)

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Abstract

During the solid-phase synthesis of a peptide fragment derived from the cancer protein NY-ESO-1 incorporating a solubilising arginine tag, a significant by-product was obtained that lacked the arginine tag. The formation of this by-product (and others) was highly dependant on the quality of the resin used and was completely removed when the resin was synthesized ‘in house’.

Key words

solid-phase - resins - HMBA linker - arginine tag

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11

Harris, P. W. R.; Brimble, M. A. manuscript in preparation.

15

Reaction of Fmoc-Arg(Pbf)-OH with TFA-TIS-H2O (95:2.5:2.5, v/v/v) gave identical HPLC and mass spectra to 6.

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Kent, S. B. H. personal communication.

23

According to reference 2, resins that swell less than 7 mL/g in CH2Cl2 should be rejected. For commercially obtained Wang, Rink Amide AM, and 2-Cl trityl reins used here, the swelling was 6.1, 5 and 4.5 mL/g, respectively, while for the ‘in house’ reins 16 and 17, the swelling was 9 and 9.7 mL/g, respectively.