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Synthesis of Sulfonimidamide-Based Amino Acid Building Blocks with Orthogonal Protecting Groups
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.ORCID iD: 0000-0002-8344-2415
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
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2019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 1045-1057Article in journal (Refereed) Published
Abstract [en]

Herein, we report the synthesis of novel sulfonimidamides (SIAs) based on amino acid building blocks using a one-pot method from tert-butyldiphenylsilyl-protected (TBDPS) sulfonamides, as well as exploration of orthogonal deprotection strategies. Among the several protecting groups investigated, TBDPS showed higher conversion, allowed UV detection and simple diastereomeric separation; in particular in combination with amino acid tert-butyl esters. Moreover, we applied the present method to synthesize cyclic five-membered acyl sulfonimidamides in two steps. The described synthesis of SIA-based amino acid building blocks in combination with the orthogonal protection groups provide access to unnatural amino acid building blocks useful for further incorporation into larger molecules, such as peptide-based transition-state analogues and peptidomimetics. The chirality of the SIA group, as well as its additional point of diversity provided by the extra NH group, creates opportunities for the development of unique compound libraries that explore new chemical space, which is of considerable importance for the pharmaceutical and agrochemical industry.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. no 5, p. 1045-1057
Keywords [en]
Sulfonimidamides, Sulfonamides, Protecting groups, Amino acids, Peptidomimetics
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-378383DOI: 10.1002/ejoc.201801541ISI: 000458273900019OAI: oai:DiVA.org:uu-378383DiVA, id: diva2:1293782
Available from: 2019-03-05 Created: 2019-03-05 Last updated: 2019-03-05Bibliographically approved

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Chinthakindi, Praveen K.Benediktsdottir, AndreaZamaratski, EdouardSandström, Anja

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