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

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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Abstract

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.

Original language	English
Pages (from-to)	130–133
Number of pages	4
Journal	Organic Letters
Volume	25
Issue number	1
Early online date	22 Dec 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c03931
Publication status	Published - 13 Jan 2023

Bibliographical note

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 KBLicence: Unspecified

Cite this

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title = "Propargylamine Amino Acids as Constrained Ne-Substituted Lysine Mimetics",

abstract = "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.",

author = "{Van Holsbeeck}, Kevin and Mathias Elsocht and Steven Ballet",

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doi = "10.1021/acs.orglett.2c03931",

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N2 - 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.

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

Abstract

Bibliographical note

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

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Propargylamine Amino Acids as Constrained Ne-Substituted Lysine Mimetics

Abstract

Bibliographical note

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Projects

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

Cite this