Succinic acid The dominant search intent appears to be understanding the role and applications of N-Hydroxysuccinimide (NHS) in peptide chemistry and related bioconjugation techniquesNHS-palmitic acid.
Tier 1:
* search_keyword: NHS peptide
* Core Entities: N-Hydroxysuccinimide (NHS), peptide, NHS ester
* High-Relevance Phrases: peptide synthesis, peptide coupling, covalent bonding, amine reactive, bioconjugation, activated esters
Tier 2:
* Entities/Concepts: Succinic acid, Sulfo-NHS, N-Acylsaccharins, PEG NHS ester, NHS FlexiBind beads, NHS-Activated Sepharose, Thio-NHS esters, N-Hydroxysuccinimide Esters
* Attributes/Functions: coupling reagent, labeling, modification, purification, active esters, site-selective, orthogonal targeting
* Related Terms: N-\u7fa5\u57fa\u7425\u73c0\u91af\u4e9e\u80fa (Chinese for N-Hydroxysuccinimide), carbodiimide method, primary amines
Tier 3:
* Specific product names (e.gThe Use of Esters of N-Hydroxysuccinimide in Peptide Synthesis., Methyl-PEG12-NHS, NHS-palmitic acid, NHS-PEG-RGD), clinical applications of C-peptide, specific research papers/authors, removal of NHS leftovers (more specific problem than general application)N-Hydroxysuccinimide - Wikipedia.
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N-Hydroxysuccinimide (NHS), often referred to as NHS peptide chemistry, plays a crucial role in modern biochemical research and development. At its core, NHS is a reagent used to create highly reactive NHS esters from carboxylic acid groupsNHS-PEG-RGD, PEG Linker. These activated esters are pivotal for forming stable covalent bonds with primary amines, a fundamental reaction in peptide synthesis, bioconjugation, and the modification of biomoleculesThe Use of Esters of N-Hydroxysuccinimide in Peptide Synthesis. Understanding how NHS facilitates these reactions is key to developing new therapeutic agents, diagnostic tools, and advanced materials.
N-Hydroxysuccinimide itself is a white solid with the chemical formula (CH₂CO)₂NOH作者：M Mentinova·2012·被引用次数：35—Covalent modification of primary amines in solution withNHSand sulfo-NHSbased reagents is a commonly applied bioconjugation technique.. Its utility in peptide modification stems from its ability to form activated estersN-Hydroxysuccinimide (NHS) isan organic compound with the formula (CH 2 CO) 2 NOH. It is a white solid that is used as a reagent for preparing active esters .... When a carboxylic acid is reacted with NHS, typically in the presence of a coupling agent like a carbodiimide (e.N-Hydroxysuccinimideg作者：GW Anderson·1964·被引用次数：1687—Thio-NHS esters are non-innocent protein acylating reagents. Nature Communications 2025, 16 (1) https://doi.org/10.1038/s41467-025-60527-5. Igor V. Krasylov ...., DCC or EDC), it forms an N-hydroxysuccinimide ester.NHS-Activated Sepharose 4 Fast Flow resin This NHS ester is significantly more reactive towards nucleophiles, particularly the amine groups found on peptides and proteins, than the original carboxylic acid.作者：M Mentinova·2012·被引用次数：35—Covalent modification of primary amines in solution withNHSand sulfo-NHSbased reagents is a commonly applied bioconjugation technique.
The reaction proceeds via nucleophilic acyl substitution. The amine nitrogen attacks the carbonyl carbon of the NHS ester, leading to the formation of a stable amide bond (a peptide bond if reacting with a peptide's N-terminus or lysine side chain) and releasing N-hydroxysuccinimide as a leaving group.Glen Report 32-26: Technical Brief - NHS Esters This process is highly efficient and is a cornerstone of techniques for labeling peptides with fluorescent dyes, biotin, or other reporter molecules.Peptide labeling with lanthanide-NHS-ester-DOTA ...
The NHS ester chemistry is indispensable for various applications involving peptides:
* Peptide Coupling: In peptide synthesis, NHS esters can be used to activate carboxyl groups for coupling with amine-containing molecules, facilitating chain elongation or the introduction of specific functionalities. While solid-phase peptide synthesis (SPPS) often employs other activation methods, NHS esters are valuable for solution-phase couplings and for modifying pre-synthesized peptides.
* Bioconjugation: This is perhaps the most widespread application. NHS esters are used to conjugate peptides to a vast array of other molecules, including proteins, antibodies, surfaces (like beads or microplates), nanoparticles, and polymers (such as PEG). This allows researchers to attach peptides to specific targets for detection, immobilization, or to confer new propertiesN-羥基琥珀醯亞胺（英語：N-Hydroxysuccinimide，NHS）是一種分子式為C4H5NO3的有機化合物，有較弱的酸性，對皮膚、眼睛和黏膜有刺激性。. For instance, NHS-PEG derivatives are used to improve the pharmacokinetics of therapeutic peptides.
* Labeling: Peptides are frequently labeled with fluorescent probes, biotin for detection via streptavidin, or other tags using NHS ester chemistry作者：Y Shan·2008·被引用次数：65—The biological activities of QDs conjugates are maintained and give superior results in cell labeling. These results are encouraging regarding .... This is crucial for techniques like enzyme-linked immunosorbent assays (ELISAs), Western blotting, and fluorescence microscopy.NHS is the most common type of activated esters. Usual modifications are fluorescent labels, fluorescence quenchers, and other reporter groups.
* Immobilization: NHS-Activated Sepharose and similar resins are widely used to immobilize peptides or proteins. The amine coupling chemistry allows for the stable attachment of peptides to the resin, which can then be used for affinity purification, solid-phase assays, or creating functionalized surfaces.N-Hydroxysuccinimide (NHS) isan organic compound with the formula (CH 2 CO) 2 NOH. It is a white solid that is used as a reagent for preparing active esters ...
While NHS itself is common, several variations exist to fine-tune reactivity and solubility:
* Sulfo-NHS (Sulfosuccinimide): These esters are more water-soluble than standard NHS esters, making them particularly useful for labeling biomolecules in aqueous solutions without the need for organic co-solvents, which can sometimes denature sensitive proteins.N Hydroxysuccinimide - an overview
* Thio-NHS Esters: These are a class of protein acylating reagents with distinct reactivity profiles, offering alternative options for specific bioconjugation strategies.
Despite its widespread use, working with NHS esters requires attention to certain details:
* Hydrolysis: NHS esters are susceptible to hydrolysis in aqueous solutions, especially at higher pH.Insulin-like growth factor 1 (IGF-1) is a peptide hormone, very similar to insulin. It is a major growth factor, which is synthesised by most cells and tissues. This can lead to the loss of the activated ester and reduced labeling efficiency.C-peptide Therefore, reactions are typically carried out under controlled pH conditions and often with fresh solutions.
* By-product Removal: After the conjugation reaction, excess NHS and any unreacted NHS ester need to be removedN-Hydroxysuccinimide. Various purification methods, such as size-exclusion chromatography or dialysis, are employed for this purposeN-羥基琥珀醯亞胺. Research continues into methods that minimize by-products or facilitate their easier removal.
* Specificity: While NHS esters primarily react with primary amines (N-terminus and lysine side chains), under certain conditions, they can react with other nucleophilic groups. Careful control of reaction stoichiometry and conditions is necessary to ensure high specificity.N-Hydroxysuccinimide (NHS) esters are reactive species which couple with amines efficiently. This type of activated esters is particularly suitable for the ...
In summary, N-Hydroxysuccinimide and its derived esters are foundational tools in the realm of peptide chemistry and bioconjugation. Their ability to efficiently activate carboxyl groups for covalent linkage with amines underpins numerous applications in research, diagnostics, and the development of novel therapeutics.
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