Communication
Labeling and Protecting N-Terminal Protein Positions by β-Peptidyl Aminopeptidase-Catalyzed Attachment of β-Amino-Acid Residues – Insulin as a First Example
Beata Kolesinska,
Joanna Wasko,
Zbigniew Kaminski,
Birgit Geueke,
Hans-Peter E. Kohler,
Dieter Seebach,
Beata Kolesinska
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
This research work was partially supported by TUL Grants I-18/501/6245/pl1 and I-18/501/6255/pl1.Search for more papers by this authorJoanna Wasko
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
Parts of the projected PhD thesis of J. W. are described herein.Search for more papers by this authorZbigniew Kaminski
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
This research work was partially supported by TUL Grants I-18/501/6245/pl1 and I-18/501/6255/pl1.Search for more papers by this authorBirgit Geueke
Department of Environmental Microbiology, Eawag, Swiss Federal Institute of Aquatic Science and Technology, Überlandstrasse 133, 8600 Dübendorf, Switzerland
Search for more papers by this authorHans-Peter E. Kohler
Department of Environmental Microbiology, Eawag, Swiss Federal Institute of Aquatic Science and Technology, Überlandstrasse 133, 8600 Dübendorf, Switzerland
Search for more papers by this authorDieter Seebach
Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland
Search for more papers by this authorBeata Kolesinska,
Joanna Wasko,
Zbigniew Kaminski,
Birgit Geueke,
Hans-Peter E. Kohler,
Dieter Seebach,
Beata Kolesinska
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
This research work was partially supported by TUL Grants I-18/501/6245/pl1 and I-18/501/6255/pl1.Search for more papers by this authorJoanna Wasko
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
Parts of the projected PhD thesis of J. W. are described herein.Search for more papers by this authorZbigniew Kaminski
Institute of Organic Chemistry, Technical University of Łodz, Zeromskiego 116, PL-90-924 Łodz, Poland
This research work was partially supported by TUL Grants I-18/501/6245/pl1 and I-18/501/6255/pl1.Search for more papers by this authorBirgit Geueke
Department of Environmental Microbiology, Eawag, Swiss Federal Institute of Aquatic Science and Technology, Überlandstrasse 133, 8600 Dübendorf, Switzerland
Search for more papers by this authorHans-Peter E. Kohler
Department of Environmental Microbiology, Eawag, Swiss Federal Institute of Aquatic Science and Technology, Überlandstrasse 133, 8600 Dübendorf, Switzerland
Search for more papers by this authorDieter Seebach
Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH-Zürich, Hönggerberg HCI, Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland
Search for more papers by this authorDedicated to Elias J. Corey on the occasion of his 90th birthday
Abstract
We have shown for the first time that a natural protein (human insulin) can be acylated at the N-terminus with a β-amino acid (H-β3hAla-), in a process catalyzed by the β-peptidyl aminopeptidase 3-2W4-BapA. This selective modification, which could also be applied for protein labeling and tagging, should be generally useful, also to protect peptides and proteins from attack by common aminopeptidases.
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