Automated Synthesis Protocol of Sequence‐Defined Oligo‐Urethane‐Amides Using Thiolactone Chemistry. Issue 1 (19th November 2018)

• Record Type: Journal Article
• Authors: Holloway, Joshua O.; Mertens, Chiel; Du Prez, Filip E.; Badi, Nezha
• Is Part Of: Macromolecular rapid communications. Volume 40:Issue 1(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2018-11-19
• Subjects: automated synthesis -- sequence‐controlled polymers -- solid‐phase -- thiolactone; Macromolecules -- Periodicals; Polymers -- Periodicals; Chemistry -- Periodicals; 547.705
• DOI: 10.1002/marc.201800685
• Languages: English
• ISSNs: 1022-1336

Abstract

Abstract: An automated, iterative protocol for the synthesis of multifunctional, sequence‐defined oligo‐urethane‐amides using thiolactone chemistry is reported. Here, sequenced functionalization of the backbone is easily introduced using commercially available primary amines. The chemistry is carried out on solid phase using different supports for better optimization of the synthetic protocol and in order to demonstrate the versatility of the approach. This technique is very effective for iterative synthesis and solid‐phase chemistry and enables the exploration of full automation of this approach using a robotic peptide synthesizer. As a result, this automated protocol allows for the synthesis of a sequence‐defined nonamer of high purity. Abstract : Thiolactone chemistry is performed in a manual and automated approach for the preparation of sequence‐defined oligomers. Various functionalities are introduced via the use of different amines. Three resins usually used for peptide synthesis and cleavable in different acidic conditions are tested and demonstrate the versatility of the methodology, leading to the formation of a nonamer with high purity.