An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides

Yik‐Hoi Yeung; Pak‐Lun Lam; Waygen Thor; Hei‐Yui Kai; Tsz‐Lam Cheung; Yue Wu; Ga‐Lai Law; Nicholas J. Long; Ka‐Leung Wong

doi:10.1002/cmtd.202400053

An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides

Yik‐Hoi Yeung, Pak‐Lun Lam, Waygen Thor, Hei‐Yui Kai, Tsz‐Lam Cheung, Yue Wu^*, Ga‐Lai Law^*, Nicholas J. Long^*, Ka‐Leung Wong^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

1 Citation (Scopus)

Abstract

1,4,7-triazacyclononane (TACN) derivatives play important roles in various metal-based biomedical applications. However, the unmanageable functionalization of TACN remains a long-standing challenge to yield useful partially substituted building blocks. Herein, by utilizing nitrobenzoxadiazole (NBD) as a thiol-liable protecting group for secondary amines, a bis-NBD-substituted TACN was obtained as the first example in the preparation of partially substituted TACN without strict stoichiometric control and column chromatography. Upon facile deprotection of NBD using solid-phase synthesis, a series of TACN-peptide conjugates with different bioactive peptides and chelating units were derivatized from the TACN building block, demonstrating the potential widespread application of this work.

Original language	English
Article number	e202400053
Number of pages	5
Journal	Chemistry-Methods
Volume	5
Issue number	5
Early online date	3 Feb 2025
DOIs	https://doi.org/10.1002/cmtd.202400053
Publication status	Published - May 2025

User-Defined Keywords

1,4,7-Triazacyclononane (TACN)
nitrobenzoxadiazole (NBD)
peptide conjugates
Positron Emission Tomography (PET)
protecting group

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/cmtd.202400053

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title = "An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides",

abstract = "1,4,7-triazacyclononane (TACN) derivatives play important roles in various metal-based biomedical applications. However, the unmanageable functionalization of TACN remains a long-standing challenge to yield useful partially substituted building blocks. Herein, by utilizing nitrobenzoxadiazole (NBD) as a thiol-liable protecting group for secondary amines, a bis-NBD-substituted TACN was obtained as the first example in the preparation of partially substituted TACN without strict stoichiometric control and column chromatography. Upon facile deprotection of NBD using solid-phase synthesis, a series of TACN-peptide conjugates with different bioactive peptides and chelating units were derivatized from the TACN building block, demonstrating the potential widespread application of this work.",

keywords = "1,4,7-Triazacyclononane (TACN), nitrobenzoxadiazole (NBD), peptide conjugates, Positron Emission Tomography (PET), protecting group",

author = "Yik‐Hoi Yeung and Pak‐Lun Lam and Waygen Thor and Hei‐Yui Kai and Tsz‐Lam Cheung and Yue Wu and Ga‐Lai Law and Long, {Nicholas J.} and Ka‐Leung Wong",

note = "Publisher Copyright: {\textcopyright} 2024 The Author(s). Chemistry - Methods published by Chemistry Europe and Wiley-VCH GmbH.",

year = "2025",

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doi = "10.1002/cmtd.202400053",

language = "English",

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T1 - An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides

AU - Yeung, Yik‐Hoi

AU - Lam, Pak‐Lun

AU - Thor, Waygen

AU - Kai, Hei‐Yui

AU - Cheung, Tsz‐Lam

AU - Wu, Yue

AU - Law, Ga‐Lai

AU - Long, Nicholas J.

AU - Wong, Ka‐Leung

PY - 2025/5

Y1 - 2025/5

N2 - 1,4,7-triazacyclononane (TACN) derivatives play important roles in various metal-based biomedical applications. However, the unmanageable functionalization of TACN remains a long-standing challenge to yield useful partially substituted building blocks. Herein, by utilizing nitrobenzoxadiazole (NBD) as a thiol-liable protecting group for secondary amines, a bis-NBD-substituted TACN was obtained as the first example in the preparation of partially substituted TACN without strict stoichiometric control and column chromatography. Upon facile deprotection of NBD using solid-phase synthesis, a series of TACN-peptide conjugates with different bioactive peptides and chelating units were derivatized from the TACN building block, demonstrating the potential widespread application of this work.

AB - 1,4,7-triazacyclononane (TACN) derivatives play important roles in various metal-based biomedical applications. However, the unmanageable functionalization of TACN remains a long-standing challenge to yield useful partially substituted building blocks. Herein, by utilizing nitrobenzoxadiazole (NBD) as a thiol-liable protecting group for secondary amines, a bis-NBD-substituted TACN was obtained as the first example in the preparation of partially substituted TACN without strict stoichiometric control and column chromatography. Upon facile deprotection of NBD using solid-phase synthesis, a series of TACN-peptide conjugates with different bioactive peptides and chelating units were derivatized from the TACN building block, demonstrating the potential widespread application of this work.

KW - 1,4,7-Triazacyclononane (TACN)

KW - nitrobenzoxadiazole (NBD)

KW - peptide conjugates

KW - Positron Emission Tomography (PET)

KW - protecting group

UR - http://www.scopus.com/inward/record.url?scp=85216950709&partnerID=8YFLogxK

U2 - 10.1002/cmtd.202400053

DO - 10.1002/cmtd.202400053

M3 - Journal article

SN - 2628-9725

VL - 5

JO - Chemistry-Methods

JF - Chemistry-Methods

IS - 5

M1 - e202400053

ER -

An Efficient Solid‐Phase Synthetic Approach to Prepare TACN‐Functionalized Peptides

Abstract

User-Defined Keywords

UN SDGs

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