酸⋅⋅⋅胺超分子合成器用于调整氨基酸基基的氨基酸的特性
Eleonora Veronese1, Claudia Pigliacelli1, Greta Bergamaschi2
1Department of Chemistry, Materials and Chemical Engineering "Giulio Natta", Politecnico di Milano, via Luigi Mancinelli 7, 20131, Milan, Italy.
Chemistry (Weinheim an der Bergstrasse, Germany)
|July 12, 2023
概括
研究人员使用Fmoc-pentafluorophenylalanine和benzamide探索了超分子水凝. 通过结合形成共同晶体,可以调整水凝的特性,并可控制生物活性分子的释放.
科学领域:
- 超分子化学 超分子化学
- 材料科学 材料科学 材料科学
- 生物医学工程 生物医学工程
背景情况:
- 基于N-Fmoc-l-phenylalanine衍生物的超分子水凝在材料和生物医学领域越来越重要.
- 预测和控制水凝特性仍然是一个挑战.
- 胺是一种非凝剂,可以通过键与氨基酸衍生物相互作用.
研究的目的:
- 为了研究Fmoc-pentafluorophenylalanine (1) 在本扎米德 (2) 的存在下自我组装的情况.
- 了解共结晶如何影响超分子凝的特性.
- 探索晶体工程在设计功能性水凝方面的潜力.
主要方法:
- 合成和表征Fmoc-pentafluorophenylalanine和胺胺.
- 在有机溶剂中的联合结晶研究.
- 使用结构,光谱和热分析,在水性介质中形成和描述水凝.
主要成果:
- (1) 和 (2) 的等分混合物通过酸⋅⋅⋅胺异构分子超分子合成,在有机溶剂中形成1:1的共同晶体.
- 在水性介质中以1:1的比例混合 (1) 和 (2) 形成的水凝中发现了相同的超分子合成物.
- 鉴定证实了水凝网络中共晶体结构的存在.
结论:
- 基于氨基酸的水凝的特性可以通过将凝器纳入共同晶体结构来调节.
- 晶体工程提供了一种控制水凝特性的策略.
- 这种方法对于开发用于延迟释放生物活性分子的水凝有效.
相关概念视频
01:28Amides to Carboxylic Acids: Hydrolysis
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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.4K
01:29Preparation of Amides
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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01:19Amines to Amides: Acylation of Amines
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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.5K
01:21Basicity of Aliphatic Amines
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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
5.9K
01:07Acid Halides to Amides: Aminolysis
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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
2.9K
01:19Structure of Amines
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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
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