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2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate

  CAS No.: 178106-34-8   Cat No.: BADC-00616 4.5  

2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate is an NHS ester ADC linker enabling efficient conjugation through hydroxyl groups, promoting stable antibody-payload linkage and enhanced drug release control in ADCs.

2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate

Structure of 178106-34-8

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ADC Linker
Molecular Formula
C7H9NO5
Molecular Weight
187.15
Shipping
Room temperature

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Synonyms
(2,5-dioxopyrrolidin-1-yl) 3-hydroxypropanoate
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-hydroxypropanoate
Canonical SMILES
OQNCXASDINIDFX-UHFFFAOYSA-N
InChI
InChI=1S/C7H9NO5/c9-4-3-7(12)13-8-5(10)1-2-6(8)11/h9H,1-4H2
InChIKey
OQNCXASDINIDFX-UHFFFAOYSA-N
Shipping
Room temperature

2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate, commonly known as 3, is a versatile chemical compound widely used in synthetic organic chemistry. One of its primary applications is in the synthesis of ester derivatives. It serves as an efficient esterifying agent due to its ability to react with various carboxylic acids, resulting in the formation of esters and amides. This makes it invaluable in the development of pharmaceuticals, where ester linkages play a crucial role in modifying drug solubility, stability, and release profiles. The use of this compound for esterification maximizes yields and minimizes by-products, thus enhancing the purity and efficacy of the final pharmaceutical product.

Another significant application of 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate is in peptide synthesis. Peptide bonds, which are essential for the formation of proteins and biologically active peptides, can be formed efficiently using this compound. Its reactive hydroxyl group allows it to facilitate the formation of strong amide linkages between amino acids. This capability is particularly important in the field of protein engineering and drug design, where precise peptide sequences are required to develop therapeutic proteins and peptides. The reliable performance of 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate in these synthetic processes makes it a preferred reagent among biochemists and molecular biologists.

In addition to its uses in ester and peptide synthesis, 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate is also employed in the development of biodegradable polymers. Its ability to form ester bonds with various polymeric chains can be harnessed to create environmentally friendly materials. These biodegradable polymers find applications in medical devices, drug delivery systems, and sustainable packaging solutions. By promoting the breakdown of polymers into non-toxic by-products, this compound contributes to reducing the environmental impact of plastic waste, aligning industrial practices with ecological sustainability goals.

Finally, 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate is used as a key intermediate in the synthesis of various heterocyclic compounds. Heterocycles are integral structural components in many natural products, pharmaceuticals, and agrochemicals. The introduction of the dioxopyrrolidinyl group through the use of this compound enhances the chemical reactivity and stability of heterocyclic frameworks. Researchers leverage this property to develop novel heterocyclic scaffolds with desirable biological and physicochemical properties. The versatility and reliability of 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate in forming complex heterocyclic structures illustrate its foundational role in innovative chemical research and development.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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Historical Records: m-PEG10-COOH | 2,5-Dioxopyrrolidin-1-yl 3-((3-((3-(trityloxy)propanoyl)oxy)propanoyl)oxy)propanoate | 2,5-Dioxopyrrolidin-1-Yl 1-Bromo-3-Methyl-2-Oxo-6,9,12,15-Tetraoxa-3-Azaoctadecan-18-Oate | 2,5-dioxopyrrolidin-1-yl 2-(dimethylamino)-4-(pyridin-2-yldisulfanyl)butanoate | DBCO-C6-NHS ester | BrCH2CONH-PEG8-NHS ester | Labetuzumab govitecan | Azido-PEG5-alcohol | 6-(Boc-amino)hexyl bromide | Acetylene-linker-Val-Cit-PABC-MMAE | 2,5-Dioxopyrrolidin-1-yl 3-Hydroxypropanoate
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