Utilization of a Branched Late-Stage Clickable Biotinylated Chassis on the Example of a Pittsburgh B Analogue

T. Moritz Weber; Pelin Özdüzenciler; Gültekin Tamgüney; Jörg Pietruszka

doi:10.1021/acs.orglett.4c02527

Utilization of a Branched Late-Stage Clickable Biotinylated Chassis on the Example of a Pittsburgh B Analogue

T. Moritz Weber
, Pelin Özdüzenciler
, Gültekin Tamgüney
, Jörg Pietruszka

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Biotinylation is probably the most frequent and practically useful modification of molecules to facilitate selective and highly affine binding to (strept)avidin for immobilization, enrichment, and purification for further (bio)chemical or (bio)physical investigations. We present a protecting-group-free synthesis of a branched biotin bis-azide that enables dual-payload late-stage functionalization with arbitrary alkynes via click chemistry. Utility of the chassis is briefly showcased on the example of a valuable Pittsburgh B analogue, which binds pathological protein aggregates, commonly found in neurodegenerative diseases.

Original language	English
Pages (from-to)	6771-6775
Journal	Organic letters
Volume	26
Issue number	31
Early online date	25 Jul 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c02527
Publication status	Published - 9 Aug 2024
Externally published	Yes

Funding

We thank the Ju\u0308rgen Manchot Foundation for project funding (doctoral scholarship to T.M.W.), the Heinrich Heine University Du\u0308sseldorf as well as the Forschungszentrum Ju\u0308lich (FZJ) for their ongoing support, and Alexandra Leyens (FZJ) for initial experiments.

Funders
Jürgen Manchot Foundation
Heinrich Heine University
Alexandra Leyens
FZJ

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10.1021/acs.orglett.4c02527Licence: CC BY

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AU - Pietruszka, Jörg

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ER -

Utilization of a Branched Late-Stage Clickable Biotinylated Chassis on the Example of a Pittsburgh B Analogue

Abstract

Funding

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