Impact of β-perfluoroalkyl substitution of proline on the proteolytic stability of its peptide derivatives

Author:

Chernykh Anton V.12,Aloshyn Danylo3,Kuchkovska Yuliya O.1,Daniliuc Constantin G.4ORCID,Tolmachova Nataliya A.1,Kondratov Ivan S.15,Zozulya Sergey3,Grygorenko Oleksandr O.12ORCID,Haufe Günter46ORCID

Affiliation:

1. Enamine Ltd., Chervonotkatska Street 78, Kyïv 02094, Ukraine

2. Taras Shevchenko National University of Kyïv, Volodymyrska Street 60, Kyïv 01601, Ukraine

3. Bienta/Enamine Ltd., Chervonotkatska Street 78, Kyïv 02094, Ukraine

4. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany

5. V.P. Kukhar Institute of Bioorganic Chemistry & Petrochemistry, National Academy of Sciences of, Ukraine, Murmanska Street 1, Kyïv 02660, Ukraine

6. Cells-in-Motion Cluster of Excellence, Universität Münster, Waldeyerstraße 15, 48149 Münster, Germany

Abstract

The synthesis of all enantiopure N-Boc-protected β-CF3- and β-C2F5-prolines and the stability of their model dipeptide derivatives towards proteolytic degradation are reported.

Funder

Deutsche Forschungsgemeinschaft

Enamine

Ministry of Education and Science of Ukraine

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

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