Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach

Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regiosel...
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Autor*in:	Jo Sing Julia Tang [verfasserIn] Kristin Schade [verfasserIn] Lucas Tepper [verfasserIn] Sany Chea [verfasserIn] Gregor Ziegler [verfasserIn] Ruben R. Rosencrantz [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2020

Schlagwörter:	carbohydrates glycosides glycosylamines design of experiments (DoE) microwave chemistry amination

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 25(2020), 21, p 5121
Übergeordnetes Werk:	volume:25 ; year:2020 ; number:21, p 5121

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules25215121

Katalog-ID:	DOAJ009647252

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authorswithroles_txt_mv	Jo Sing Julia Tang @@aut@@ Kristin Schade @@aut@@ Lucas Tepper @@aut@@ Sany Chea @@aut@@ Gregor Ziegler @@aut@@ Ruben R. Rosencrantz @@aut@@
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callnumber-first	Q - Science
author	Jo Sing Julia Tang
spellingShingle	Jo Sing Julia Tang misc QD241-441 misc carbohydrates misc glycosides misc glycosylamines misc design of experiments (DoE) misc microwave chemistry misc amination misc Organic chemistry Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach
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topic_title	QD241-441 Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach carbohydrates glycosides glycosylamines design of experiments (DoE) microwave chemistry amination
topic	misc QD241-441 misc carbohydrates misc glycosides misc glycosylamines misc design of experiments (DoE) misc microwave chemistry misc amination misc Organic chemistry
topic_unstemmed	misc QD241-441 misc carbohydrates misc glycosides misc glycosylamines misc design of experiments (DoE) misc microwave chemistry misc amination misc Organic chemistry
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title	Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach
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title_full	Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach
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author_browse	Jo Sing Julia Tang Kristin Schade Lucas Tepper Sany Chea Gregor Ziegler Ruben R. Rosencrantz
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title_sort	optimization of the microwave assisted glycosylamines synthesis based on a statistical design of experiments approach
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title_auth	Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach
abstract	Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regioselective amination conditions of different saccharides. Amination reactions were performed according to Kochetkov and Likhoshertov and accelerated by microwave irradiation. We optimized the synthesis of glycosylamines for <i<N</i<-acetyl-<span style="font-variant: small-caps;"<d</span<-galactosamine, <span style="font-variant: small-caps;"<d</span<-lactose, <span style="font-variant: small-caps;"<d</span<-glucuronic acid and <span style="font-variant: small-caps;"<l</span<-(−)-fucose using the design of experiments (DoE) approach. DoE enables efficient optimization with limited number of experimental data. A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. There is strong indication that high temperatures are favored for the amination reaction.
abstractGer	Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regioselective amination conditions of different saccharides. Amination reactions were performed according to Kochetkov and Likhoshertov and accelerated by microwave irradiation. We optimized the synthesis of glycosylamines for <i<N</i<-acetyl-<span style="font-variant: small-caps;"<d</span<-galactosamine, <span style="font-variant: small-caps;"<d</span<-lactose, <span style="font-variant: small-caps;"<d</span<-glucuronic acid and <span style="font-variant: small-caps;"<l</span<-(−)-fucose using the design of experiments (DoE) approach. DoE enables efficient optimization with limited number of experimental data. A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. There is strong indication that high temperatures are favored for the amination reaction.
abstract_unstemmed	Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regioselective amination conditions of different saccharides. Amination reactions were performed according to Kochetkov and Likhoshertov and accelerated by microwave irradiation. We optimized the synthesis of glycosylamines for <i<N</i<-acetyl-<span style="font-variant: small-caps;"<d</span<-galactosamine, <span style="font-variant: small-caps;"<d</span<-lactose, <span style="font-variant: small-caps;"<d</span<-glucuronic acid and <span style="font-variant: small-caps;"<l</span<-(−)-fucose using the design of experiments (DoE) approach. DoE enables efficient optimization with limited number of experimental data. A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. There is strong indication that high temperatures are favored for the amination reaction.
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title_short	Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach
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A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. 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Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach

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