Propargylamine Amino Acids as Constrained Ne-Substituted Lysine Mimetics

Kevin Van Holsbeeck; Mathias Elsocht; Steven Ballet

doi:10.1021/acs.orglett.2c03931

Propargylamine Amino Acids as Constrained Ne-Substituted Lysine Mimetics

Kevin Van Holsbeeck, Mathias Elsocht, Steven Ballet

Onderzoeksoutput: Article › peer review

2 Citaten (Scopus)

63 Downloads (Pure)

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Herein, alkylated propargylamines are reported as constrained lysine mimetics and constructed in a single step using a copper(I)-catalyzed A3-coupling reaction. Using multiple secondary amines, the reaction allowed the generation of a structurally diverse set of N-Fmoc protected amino acid derivatives. In addition, the A3-reaction was applied on solid phase via the assembly of short model tripeptides. Moreover, the internal alkyne moiety allowed further functionalization toward novel 1,4,5-trisubstituted 1,2,3-triazole-based amino acids.

Originele taal-2	English
Pagina's (van-tot)	130–133
Aantal pagina's	4
Tijdschrift	Organic Letters
Volume	25
Nummer van het tijdschrift	1
Vroegere onlinedatum	22 dec. 2022
DOI's	https://doi.org/10.1021/acs.orglett.2c03931
Status	Published - 13 jan. 2023

Bibliografische nota

Funding Information:
K.V.h. and S.B. thank the Research Foundation Flanders (FWO Vlaanderen) for providing a PhD fellowship to K.V.h. (FWOTM931). S.B. thanks the Research Council of the Vrije Universiteit Brussel for financial support through the Strategic Research Programme (SRP50). Giulia Atza is acknowledged for performing preliminary work.

Publisher Copyright:
© 2022 American Chemical Society.

Copyright:
Copyright 2023 Elsevier B.V., All rights reserved.

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10.1021/acs.orglett.2c03931

Van_holsbeeck_et_al_Org_Lett_final_revisedAccepted author manuscript, 439 KBLicentie: Unspecified

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SRP50: SRP-Onderzoekszwaartepunt: Exploiting Peptides: Protein Binders, Modulators and Inhibitors for Imaging and Therapy [Exploit-PeptIT]
Ballet, S., Caveliers, V., Hernot, S., Versées, W., Vinken, M., Muyldermans, S., Devoogdt, N., Bridoux, J. & Martin, C.
1/03/19 → 30/09/25
Project: Fundamenteel

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AB - Herein, alkylated propargylamines are reported as constrained lysine mimetics and constructed in a single step using a copper(I)-catalyzed A3-coupling reaction. Using multiple secondary amines, the reaction allowed the generation of a structurally diverse set of N-Fmoc protected amino acid derivatives. In addition, the A3-reaction was applied on solid phase via the assembly of short model tripeptides. Moreover, the internal alkyne moiety allowed further functionalization toward novel 1,4,5-trisubstituted 1,2,3-triazole-based amino acids.

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Propargylamine Amino Acids as Constrained Ne-Substituted Lysine Mimetics

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SRP50: SRP-Onderzoekszwaartepunt: Exploiting Peptides: Protein Binders, Modulators and Inhibitors for Imaging and Therapy [Exploit-PeptIT]

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