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Synthesis of stapled beta3 - peptides through ring - closing metathesis

Bergman, Y.E. and Del Borgo, M.P. and Gopalan, Romila D. and Jalal, S. and Unabia, S.E. and Ciampini, M. and Clayton, D.J. and Fletcher, J.M. and Mulder, R.J. and Wilce, J.A. and Aguilar, M.I. and Perlmutter, P. (2009) Synthesis of stapled beta3 - peptides through ring - closing metathesis. Organic Letters, 11 (19). pp. 4438-4440. ISSN 1523-7060

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The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with O-allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Technology and Environment (FSTE) > School of Biological and Chemical Sciences
Depositing User: Romila Devi Gopalan
Date Deposited: 24 Sep 2013 05:02
Last Modified: 14 Oct 2013 22:04

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