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Late-stage Functionalization of Peptides and Cyclopeptides using Organozinc reagents

Vorherr, Thomas, Lewis, Ian and Schaefer, Michael (2019) Late-stage Functionalization of Peptides and Cyclopeptides using Organozinc reagents. Angewandte Chemie, 58. pp. 1-5.

Abstract

We have reported a new late-stage functionalization of small peptides and cyclopeptides using readily prepared iodotyrosine or iodophenylalanine containing peptides and performing Negishi cross-couplings with aryl-, heteroaryl- and alkyl-zinc pivalates or halides. In-silico and in-vitro determinations of membrane permeability data of the modified cyclopeptides showed that in most cases, the solubility was improved while the cell-membrane permeability was maintained by the introduction of polar pyridyl units.

Item Type: Article
Keywords: cross-coupling cyclopeptides membrane permeability organozinc peptides cross-coupling cyclopeptide membrane permeability organozinc peptides
Date Deposited: 25 May 2019 00:45
Last Modified: 25 May 2019 00:45
URI: https://oak.novartis.com/id/eprint/39057

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