Nucleophilic catalysis of carbohydrate oxime formation by anilines

Mikkel Boas Thygesen; Henrik Kofoed Munch; Jørgen Sauer; Emiliano Cló; Malene R. Jørgensen; Ole Hindsgaul; Knud Jørgen Jensen

doi:10.1021/jo902425v

Nucleophilic catalysis of carbohydrate oxime formation by anilines

Mikkel Boas Thygesen, Henrik Kofoed Munch, Jørgen Sauer, Emiliano Cló, Malene R. Jørgensen, Ole Hindsgaul, Knud Jørgen Jensen

64 Citations (Scopus)

Abstract

("Figure Presented") Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.

Original language	English
Journal	Journal of Organic Chemistry
Volume	75
Issue number	5
Pages (from-to)	1752-1755
Number of pages	4
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo902425v
Publication status	Published - 5 Mar 2010

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abstract = "({"}Figure Presented{"}) Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.",

author = "Thygesen, {Mikkel Boas} and Munch, {Henrik Kofoed} and J{\o}rgen Sauer and Emiliano Cl{\'o} and J{\o}rgensen, {Malene R.} and Ole Hindsgaul and Jensen, {Knud J{\o}rgen}",

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T1 - Nucleophilic catalysis of carbohydrate oxime formation by anilines

AU - Thygesen, Mikkel Boas

AU - Munch, Henrik Kofoed

AU - Sauer, Jørgen

AU - Cló, Emiliano

AU - Jørgensen, Malene R.

AU - Hindsgaul, Ole

AU - Jensen, Knud Jørgen

PY - 2010/3/5

Y1 - 2010/3/5

N2 - ("Figure Presented") Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.

AB - ("Figure Presented") Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.

U2 - 10.1021/jo902425v

DO - 10.1021/jo902425v

M3 - Journal article

C2 - 20131837

SN - 0022-3263

VL - 75

SP - 1752

EP - 1755

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Nucleophilic catalysis of carbohydrate oxime formation by anilines

Abstract

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