湖南韵邦生物医药有限公司
Hunan Yunbang Bio-pharmaceutical Co., Ltd.

图片展示

 服务热线:400-0909-710

搜索
中文
  • English

图片展示

新闻资讯

— NEWS —

联系我们

— CONTACT US —

全国热线:13319523173

联系电话:13319523173鲁经理 13308453923肖经理
销售部:0731-85526065 0731-85529965
外贸部:0731-85525705 13319518603梁经理
传准:0745-7695263
邮箱:ivy@hnhbsj.com
地址:湖南省怀化市洪江区工业园8号
销售处地址:湖南省长沙市岳麓区麓谷企业广场C3栋11楼

新闻分类

详细信息


A simple and efficient synthesis of the inducer IPTG(367-93-1) made for inexpensive heterologous protein production using the toe-promoter

 Introduction:

IPTG (isopropyl 1 -thio-β-D-galactopyranoside) is very frequently used to induce synthesis of heterologous proteins in Escherichiacoli in cases where transcription is controlled by the /ac-promoter.

The great cost of using large quantities of commercially produced IPTG has encouraged the investigation of simple and efficient methods for preparation of the compound. The aim of this work

was to design a synthetic route that can be easily used without any special knowledge in the field of carbohydrate synthesis. Thus the synthesis should be simple and economic, giving large

quantities of IPTG without any tedious purification steps.Therefore, we have developed a two-step procedure for the synthesis of IPTG, where chromatographic purification of the product can be omitted.

 

Result:

Alkyl l-thio-i3-D-galactoside syntheses are presented in the literature by various methods. The predominating strategy used is reaction of a thiol with a catalyst and an activated and suitably

protected sugar unit, e.g. acetobromogalactose (Helferich and Turk, 1956) and acetyl-protected O-(a-D-galactopyranosyl)trichloroimidate (Schmidt and Stumpp, 1983). Preparation and use

of these activated sugar derivatives demand skilful synthetic performance. An easier and more convenient way is to use a fully acetylated D-glycopyranose, which with a Lewis acid as a catalyst

and thiols, gives 1-thio-glycosides in high yields (Paulsen and Brenken. 1988). The stereoselectivity in these reactions for /3-glycosides depends mainly of a participating 2-O-acyl group in the sugar unit and performance at low temperature preventing acid-catalysed anomerization to a-glycosides.

The commercially available penta-O-acetyl-j3-D-galactopyranose and 2-propanethiol in dichloromethane were allowed to react at -40°C with stannous chloride as a Lewis catalyst.

After a reaction time of 8 h or overnight a yield >95% of crude isopropyl 2,3,4,6-tetra-o-acetyl-l-thio-β-D-galactopyranoside was obtained. Deacetylation with methanolic sodium methoxide and crystallization from dioxane gave pure IPTG in an overall yield of 88% in a synthetic scale giving 10 g. This procedure for synthesis can without any problems be scaled up by a factor of three. The synthesis can be completed in 2 days to a cost that is a small fraction of the commercial price.


0

A simple and efficient synthesis of the inducer IPTG(367-93-1) made for inexpensive heterologous protein production using the toe-promoter

作者:湖南韵邦生物医药有限公司 浏览: 发表时间:2021-03-11 14:04:45

 Introduction:

IPTG (isopropyl 1 -thio-β-D-galactopyranoside) is very frequently used to induce synthesis of heterologous proteins in Escherichiacoli in cases where transcription is controlled by the /ac-promoter.

The great cost of using large quantities of commercially produced IPTG has encouraged the investigation of simple and efficient methods for preparation of the compound. The aim of this work

was to design a synthetic route that can be easily used without any special knowledge in the field of carbohydrate synthesis. Thus the synthesis should be simple and economic, giving large

quantities of IPTG without any tedious purification steps.Therefore, we have developed a two-step procedure for the synthesis of IPTG, where chromatographic purification of the product can be omitted.

 

Result:

Alkyl l-thio-i3-D-galactoside syntheses are presented in the literature by various methods. The predominating strategy used is reaction of a thiol with a catalyst and an activated and suitably

protected sugar unit, e.g. acetobromogalactose (Helferich and Turk, 1956) and acetyl-protected O-(a-D-galactopyranosyl)trichloroimidate (Schmidt and Stumpp, 1983). Preparation and use

of these activated sugar derivatives demand skilful synthetic performance. An easier and more convenient way is to use a fully acetylated D-glycopyranose, which with a Lewis acid as a catalyst

and thiols, gives 1-thio-glycosides in high yields (Paulsen and Brenken. 1988). The stereoselectivity in these reactions for /3-glycosides depends mainly of a participating 2-O-acyl group in the sugar unit and performance at low temperature preventing acid-catalysed anomerization to a-glycosides.

The commercially available penta-O-acetyl-j3-D-galactopyranose and 2-propanethiol in dichloromethane were allowed to react at -40°C with stannous chloride as a Lewis catalyst.

After a reaction time of 8 h or overnight a yield >95% of crude isopropyl 2,3,4,6-tetra-o-acetyl-l-thio-β-D-galactopyranoside was obtained. Deacetylation with methanolic sodium methoxide and crystallization from dioxane gave pure IPTG in an overall yield of 88% in a synthetic scale giving 10 g. This procedure for synthesis can without any problems be scaled up by a factor of three. The synthesis can be completed in 2 days to a cost that is a small fraction of the commercial price.


A simple and efficient synthesis of the inducer IPTG(367-93-1) made for inexpensive heterologous protein production using the toe-promoter

作者:湖南韵邦生物医药有限公司 浏览: 发表时间:2021-03-11 14:04:45

 Introduction:

IPTG (isopropyl 1 -thio-β-D-galactopyranoside) is very frequently used to induce synthesis of heterologous proteins in Escherichiacoli in cases where transcription is controlled by the /ac-promoter.

The great cost of using large quantities of commercially produced IPTG has encouraged the investigation of simple and efficient methods for preparation of the compound. The aim of this work

was to design a synthetic route that can be easily used without any special knowledge in the field of carbohydrate synthesis. Thus the synthesis should be simple and economic, giving large

quantities of IPTG without any tedious purification steps.Therefore, we have developed a two-step procedure for the synthesis of IPTG, where chromatographic purification of the product can be omitted.

 

Result:

Alkyl l-thio-i3-D-galactoside syntheses are presented in the literature by various methods. The predominating strategy used is reaction of a thiol with a catalyst and an activated and suitably

protected sugar unit, e.g. acetobromogalactose (Helferich and Turk, 1956) and acetyl-protected O-(a-D-galactopyranosyl)trichloroimidate (Schmidt and Stumpp, 1983). Preparation and use

of these activated sugar derivatives demand skilful synthetic performance. An easier and more convenient way is to use a fully acetylated D-glycopyranose, which with a Lewis acid as a catalyst

and thiols, gives 1-thio-glycosides in high yields (Paulsen and Brenken. 1988). The stereoselectivity in these reactions for /3-glycosides depends mainly of a participating 2-O-acyl group in the sugar unit and performance at low temperature preventing acid-catalysed anomerization to a-glycosides.

The commercially available penta-O-acetyl-j3-D-galactopyranose and 2-propanethiol in dichloromethane were allowed to react at -40°C with stannous chloride as a Lewis catalyst.

After a reaction time of 8 h or overnight a yield >95% of crude isopropyl 2,3,4,6-tetra-o-acetyl-l-thio-β-D-galactopyranoside was obtained. Deacetylation with methanolic sodium methoxide and crystallization from dioxane gave pure IPTG in an overall yield of 88% in a synthetic scale giving 10 g. This procedure for synthesis can without any problems be scaled up by a factor of three. The synthesis can be completed in 2 days to a cost that is a small fraction of the commercial price.


A simple and efficient synthesis of the inducer IPTG(367-93-1) made for inexpensive heterologous protein production using the toe-promoter

作者:湖南韵邦生物医药有限公司 浏览: 发表时间:2021-03-11 14:04:45

 Introduction:

IPTG (isopropyl 1 -thio-β-D-galactopyranoside) is very frequently used to induce synthesis of heterologous proteins in Escherichiacoli in cases where transcription is controlled by the /ac-promoter.

The great cost of using large quantities of commercially produced IPTG has encouraged the investigation of simple and efficient methods for preparation of the compound. The aim of this work

was to design a synthetic route that can be easily used without any special knowledge in the field of carbohydrate synthesis. Thus the synthesis should be simple and economic, giving large

quantities of IPTG without any tedious purification steps.Therefore, we have developed a two-step procedure for the synthesis of IPTG, where chromatographic purification of the product can be omitted.

 

Result:

Alkyl l-thio-i3-D-galactoside syntheses are presented in the literature by various methods. The predominating strategy used is reaction of a thiol with a catalyst and an activated and suitably

protected sugar unit, e.g. acetobromogalactose (Helferich and Turk, 1956) and acetyl-protected O-(a-D-galactopyranosyl)trichloroimidate (Schmidt and Stumpp, 1983). Preparation and use

of these activated sugar derivatives demand skilful synthetic performance. An easier and more convenient way is to use a fully acetylated D-glycopyranose, which with a Lewis acid as a catalyst

and thiols, gives 1-thio-glycosides in high yields (Paulsen and Brenken. 1988). The stereoselectivity in these reactions for /3-glycosides depends mainly of a participating 2-O-acyl group in the sugar unit and performance at low temperature preventing acid-catalysed anomerization to a-glycosides.

The commercially available penta-O-acetyl-j3-D-galactopyranose and 2-propanethiol in dichloromethane were allowed to react at -40°C with stannous chloride as a Lewis catalyst.

After a reaction time of 8 h or overnight a yield >95% of crude isopropyl 2,3,4,6-tetra-o-acetyl-l-thio-β-D-galactopyranoside was obtained. Deacetylation with methanolic sodium methoxide and crystallization from dioxane gave pure IPTG in an overall yield of 88% in a synthetic scale giving 10 g. This procedure for synthesis can without any problems be scaled up by a factor of three. The synthesis can be completed in 2 days to a cost that is a small fraction of the commercial price.


A simple and efficient synthesis of the inducer IPTG(367-93-1) made for inexpensive heterologous protein production using the toe-promoter

作者:湖南韵邦生物医药有限公司 浏览: 发表时间:2021-03-11 14:04:45

 Introduction:

IPTG (isopropyl 1 -thio-β-D-galactopyranoside) is very frequently used to induce synthesis of heterologous proteins in Escherichiacoli in cases where transcription is controlled by the /ac-promoter.

The great cost of using large quantities of commercially produced IPTG has encouraged the investigation of simple and efficient methods for preparation of the compound. The aim of this work

was to design a synthetic route that can be easily used without any special knowledge in the field of carbohydrate synthesis. Thus the synthesis should be simple and economic, giving large

quantities of IPTG without any tedious purification steps.Therefore, we have developed a two-step procedure for the synthesis of IPTG, where chromatographic purification of the product can be omitted.

 

Result:

Alkyl l-thio-i3-D-galactoside syntheses are presented in the literature by various methods. The predominating strategy used is reaction of a thiol with a catalyst and an activated and suitably

protected sugar unit, e.g. acetobromogalactose (Helferich and Turk, 1956) and acetyl-protected O-(a-D-galactopyranosyl)trichloroimidate (Schmidt and Stumpp, 1983). Preparation and use

of these activated sugar derivatives demand skilful synthetic performance. An easier and more convenient way is to use a fully acetylated D-glycopyranose, which with a Lewis acid as a catalyst

and thiols, gives 1-thio-glycosides in high yields (Paulsen and Brenken. 1988). The stereoselectivity in these reactions for /3-glycosides depends mainly of a participating 2-O-acyl group in the sugar unit and performance at low temperature preventing acid-catalysed anomerization to a-glycosides.

The commercially available penta-O-acetyl-j3-D-galactopyranose and 2-propanethiol in dichloromethane were allowed to react at -40°C with stannous chloride as a Lewis catalyst.

After a reaction time of 8 h or overnight a yield >95% of crude isopropyl 2,3,4,6-tetra-o-acetyl-l-thio-β-D-galactopyranoside was obtained. Deacetylation with methanolic sodium methoxide and crystallization from dioxane gave pure IPTG in an overall yield of 88% in a synthetic scale giving 10 g. This procedure for synthesis can without any problems be scaled up by a factor of three. The synthesis can be completed in 2 days to a cost that is a small fraction of the commercial price.


版权所有(C) 湖南韵邦生物医药有限公司  湘ICP备18001567号-1

客服中心
热线电话
400-12346578
上班时间
周一到周五
二维码
在线客服
联系方式
二维码
置顶
在线客服
联系方式
全国热线
400-0909-710
电子邮箱
ivy@hnhbsj.com
销售部
13319523173 鲁经理 13308453923 肖经理
外贸部
0731-85525705 13319518603 梁经理
二维码
二维码