The CSY-protecting group in the microwave-assisted synthesis of aggregation-prone peptides

Truc Lam Pham; Jennifer Zilke; Christine Charlotte Müller; Franziska Thomas

doi:10.1039/d1cb00252j

The CSY-protecting group in the microwave-assisted synthesis of aggregation-prone peptides

RSC Chem Biol. 2022 Feb 18;3(4):426-430. doi: 10.1039/d1cb00252j. eCollection 2022 Apr 6.

Authors

Truc Lam Pham^{1

2}, Jennifer Zilke^{1

2}, Christine Charlotte Müller³, Franziska Thomas^{1

2}

Affiliations

¹ Institute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270 69120 Heidelberg Germany franziska.thomas@oci.uni-heidelberg.de.
² Centre for Advanced Materials, Heidelberg University, Im Neuenheimer Feld 225 69120 Heidelberg Germany.
³ Institute of Inorganic Chemistry, RWTH Aachen University Landoltweg 1a 52074 Aachen Germany.

Abstract

This report describes the application of cyanosulfurylide (CSY)-protected aspartatic acid building blocks in microwave-assisted synthesis of aggregation-prone protein domains. We present a synthesis of Fmoc-Asp(CSY)-OH on a multigram scale, as well as procedures for the microwave-assisted synthesis of CSY-protected peptides, and CSY cleavage in partially folded or aggregation-prone peptides.