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An Allyl Protection and Improved Purification Strategy Enables the Synthesis of Functionalized Phosphonamidate Peptides

Cramer, Jonathan and Klebe, Gerhard. (2017) An Allyl Protection and Improved Purification Strategy Enables the Synthesis of Functionalized Phosphonamidate Peptides. Synthesis, 49 (8). pp. 1857-1866.

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Official URL: https://edoc.unibas.ch/70163/

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Abstract

For modern biophysical methods such as isothermal titration calorimetry, high purity of the inhibitor of interest is indispensable. Herein, we describe a procedure for the synthesis and purification of functionalized phosphonamidate peptides that is able to generate inhibitors for the metalloprotease thermolysin for use in biophysical experiments. The method utilizes an allyl ester/alloc protection strategy and takes advantage of a fast and effective solid-phase extraction (SPE) purification step. Applying this strategy, we were able to synthesize a series of highly polar inhibitors featuring amino-and hydroxy-functionalized side chains in excellent purity.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Molekulare Pharmazie (Ernst)
UniBasel Contributors:Cramer, Jonathan
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:GEORG THIEME VERLAG KG
ISSN:0039-7881
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:16 Apr 2019 15:35
Deposited On:16 Apr 2019 15:35

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