相关实验视频

Updated: Jun 18, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

两种制备方法,用于酸含酸含酸 (SO₃H) 残留物) 的制备方法,而无需使用硫酸盐组的保护组

Yumi Sekigawa¹, Shinichi Asada¹, Yurie Ichikawa¹

¹Faculty of Pharamaceutical Sciences, Niigata University of Pharmacy and Medical and Life Sciences.

Chemical & pharmaceutical bulletin

|July 28, 2024

概括

我们开发了两种新的方法,用硫酸铁残留物合成乙烯,简化了硫制备. 这些技术可以创建复杂的分子,如PSGL-1和CCR5碎片.

科学领域:

有机化学有机化学
类化学类化学
生物化学生物化学

背景情况:

硫酸铁残留物是许多生物活性和蛋白质中发现的关键的翻译后修饰.
由于硫酸盐组的不稳定性和保护组的需要,硫酸的有效合成仍然具有挑战性.
乙烯 thioesters 是用于合成的多功能中间体,特别是用于片段凝结和原生化学结合.

研究的目的:

开发和报告两种新方法,用于制备含有硫酸铁残留物 (Tyr(SO3H)) 的乙烯 thioesters.
为了证明这些基的实用性,作为合成复杂硫的基石.
在不需要为硫酸盐部分提供保护组的情况下实现合成.

主要方法:

方法1:直接使用碳二胺在完全受保护的酸上进行二二 (Clt) 树脂上的素-9-ylmethoxycarbonyl (Fmoc) 基固相合成 (SPPS),然后用三酸 (TFA) 进行脱.
方法2:使用Fmoc-SPPS. 在NH2NH-Clt树脂上制备的化,从化中衍生出的化.
应用:合成Nα-Fmoc受保护的P-选择蛋白糖蛋白连接体1 (PSGL-1) 片段和CC-化学因子受体5 (CCR5) 的N-终端细胞外部分,使用已制备的基.

主要成果:

通过使用直接化方法,成功制备了含有1到3个Tyr(SO3H) 残留物的酸乙.
通过化方法成功制备了含有两个Tyr(SO3H) 残留的酸乙.
通过银离子介导凝结和原生化学结合 (NCL) 来合成生物相关的片段 (PSGL-1和CCR5) 证明了这些含Tyr(SO3H) 的乙的使用.

结论:

报告的方法提供了高效的合成乙与Tyr ((SO3H) 残留物的途径,没有硫酸盐保护.
这些方法广泛适用于各种硫的合成,促进了糖生物学和相关领域的进一步研究.
直接化和酸方法为构建复杂的硫酸结构提供了有价值的工具.

关键词:

含有Tyr ((SO3H) 的化物.原生化学结合原生化学结合酸阿酸是一种酸.酸乙烯 thioester 是一种酸乙烯.通过银离子介导的段凝结.这种方法是 thioesterification.

更多相关视频

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Published on: August 20, 2018

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

相关概念视频

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...

Preparation of Acid Anhydrides

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...