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Sunflower trypsin inhibitor (SFTI-1) analogues of synthetic and biological origin via N -> S acyl transfer: potential inhibitors of human Kallikrein-5 (KLK5)

Shariff, L; Zhu, Y; Cowper, B; Di, W-L; Macmillan, D; (2014) Sunflower trypsin inhibitor (SFTI-1) analogues of synthetic and biological origin via N -> S acyl transfer: potential inhibitors of human Kallikrein-5 (KLK5). TETRAHEDRON , 70 (42) 7675 - 7680. 10.1016/j.tet.2014.06.059. Green open access

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Abstract

Sunflower Trypsin Inhibitor (SFTI-1) analogues have been prepared from simple linear precursors produced either by chemical synthesis or following purification from Escherichia coli. We have shown, for the first time that these linear SFTI-1 derived peptide sequences can be converted to circular peptides via selective consecutive acyl transfer reactions, and that the products derived from synthetic and bacterial origin are identical. Preliminary analysis of the semi-synthetic SFTI-1 analogues confirmed SFTI-I10H as an inhibitor of Kallikrein-5 (KLK5) protease that could also mediate its action on human keratinocytes. The preliminary results obtained serve as a useful starting point for the biological production of SFTI-1 based, selective KLK5 inhibitors for the treatment of atopic dermatitis.

Type: Article
Title: Sunflower trypsin inhibitor (SFTI-1) analogues of synthetic and biological origin via N -> S acyl transfer: potential inhibitors of human Kallikrein-5 (KLK5)
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2014.06.059
Publisher version: http://dx.doi.org/10.1016/j.tet.2014.06.059
Additional information: Copyright © 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).
Keywords: Sunflower trypsin inhibitor, Native chemical ligation, KLK5, Atopic dermatitis
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1435158
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