Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

Anne Brinko; Christian Risinger; Annie Lambert; Ola Blixt; Cyrille Grandjean; Henrik H. Jensen

doi:10.1021/acs.orglett.9b02811

Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

Anne Brinko, Christian Risinger, Annie Lambert, Ola Blixt, Cyrille Grandjean, Henrik H. Jensen

Department of Chemistry

1 Citation (Scopus)

Abstract

Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

Original language	English
Journal	Organic Letters
Volume	21
Issue number	18
Pages (from-to)	7544-7548
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.9b02811
Publication status	Published - 20 Sept 2019

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abstract = "Here, we report on the first combined one-pot use of the two so-called {"}click reactions{"}: The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.",

author = "Anne Brinko and Christian Risinger and Annie Lambert and Ola Blixt and Cyrille Grandjean and Jensen, {Henrik H.}",

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T1 - Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

AU - Brinko, Anne

AU - Risinger, Christian

AU - Lambert, Annie

AU - Blixt, Ola

AU - Grandjean, Cyrille

AU - Jensen, Henrik H.

PY - 2019/9/20

Y1 - 2019/9/20

N2 - Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

AB - Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

U2 - 10.1021/acs.orglett.9b02811

DO - 10.1021/acs.orglett.9b02811

M3 - Letter

C2 - 31502847

SN - 1523-7060

VL - 21

SP - 7544

EP - 7548

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

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