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Synthesis of Mixed α/β2,2-Peptides by Site-Selective Ring-Opening of Cyclic Quaternary Sulfamidates

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Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja, C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain
Cite this: Org. Lett. 2015, 17, 23, 5804–5807
Publication Date (Web):November 16, 2015
https://doi.org/10.1021/acs.orglett.5b02927
Copyright © 2015 American Chemical Society

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    Abstract

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    A method for site- and stereoselective peptide modification using a cyclic sulfamidate scaffold containing peptides is described. A peptide synthesis strategy allowing the rapid generation of mixed α/β-peptides incorporating a sulfamidate residue, derived from 2-methylisoserine, has been generalized. The unique electrophilic nature of this scaffold for nucleophilic substitution at a quaternary center with total inversion of its configuration, which was demonstrated computationally, allows for site-selective conjugation with various nucleophiles, such as anomeric thiocarbohydrates and pyridines. This strategy provides rapid access to complex thioglyco-α/β-conjugates and charged α/β-peptides.

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