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Tailored Modification of Thioacrylates in a Versatile, Sequence‐Defined Procedure
Author(s) -
Holloway Joshua O.,
Aksakal Suzan,
Du Prez Filip E.,
Becer C. Remzi
Publication year - 2017
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700500
Subject(s) - thiophenol , combinatorial chemistry , sequence (biology) , mass spectrometry , context (archaeology) , chemistry , solid phase synthesis , materials science , chromatography , organic chemistry , peptide , paleontology , biochemistry , biology
A strategy for the synthesis of sequence‐defined oligomers using a selective side‐group insertion approach making use of thiophenol‐catalyzed amidation reactions is herein reported. In this context, a new thiolactone‐based, multistep, iterative protocol is designed, utilizing thioacrylates in combination with solid‐phase synthesis for step‐by‐step growth, resulting in sequence‐defined oligomers. Sequence definition and structure variation are introduced by substituting the thioacrylate side groups with a wide variety of amines. The step‐by‐step growth of the oligomers is followed by liquid chromatography–mass spectrometry and high‐resolution mass spectroscopy to determine both conversion and purity.