DTPA is diethylenetriaminepentaacetic anhydride, a bifunctional chelating agent containing two amine-reactive anhydride groups. The degradation and resorption kinetics of these unstable polymers can be designed from days to months depending on the synthesized backbone structure (Domb et al. Theodor Wieland, in Peptides: Synthesis, Structures, and Applications, 1995. Like POE, poly(anhydrides) are found to degrade via surface erosion. . 12 In uncatalyzed systems, the anhydride reacts with hydroxyl groups of the epoxy resin to produce monoesters and generates a free carboxyl group (COOH) (Figure 3.4 a).
In organic chemistry, organic acid anhydrides contain the functional group R(CO)O(CO)R'. Reaction of the sulfinamide lactone 99 with β-ketoesters gives C-acylated diketo intermediates 100, which subsequently cyclize via the condensation of the 2-amino group with a keto group to give the 1,8-naphthyridin-4-ones 101. Ethanoic anhydride is safer to use than ethanoyl chloride. Burdick, in Polymer Science: A Comprehensive Reference, 2012, The general structure of anhydride monomers used for photopolymerizations consists of a repeating hydrophobic core molecule such as sebacic acid, carboxyphenoxy propane, or carboxyphenoxy hexane with photoreactive methacrylate end groups. . It is less corrosive and not so readily hydrolysed (its reaction with water is slower). The reasons for using ethanoic anhydride rather than ethanoyl chloride include: The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot.
This work has been thoroughly reviewed through 1968.
Although this reaction can also be done with ethanoyl chloride, aspirin is manufactured by reacting 2-hydroxybenzoic acid with ethanoic anhydride at 90°C.
The mixed anhydrides were obtained from N-protected amino acids and acyl chlorides in an inert solvent in the presence of a tertiary base and were reacted without isolation at room temperature with the respective amino compounds (Fig. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780123822390000030, URL: https://www.sciencedirect.com/science/article/pii/B9780323042895100426, URL: https://www.sciencedirect.com/science/article/pii/B9780080970370000208, URL: https://www.sciencedirect.com/science/article/pii/B9780323508780000021, URL: https://www.sciencedirect.com/science/article/pii/B0080431526013711, URL: https://www.sciencedirect.com/science/article/pii/B9780080449920009172, URL: https://www.sciencedirect.com/science/article/pii/B9780123109200500024, URL: https://www.sciencedirect.com/science/article/pii/B9780121852856500257, URL: https://www.sciencedirect.com/science/article/pii/B9780444533494002272, URL: https://www.sciencedirect.com/science/article/pii/B9780123822390000121, The Immunoassay Handbook (Fourth Edition), Conjugation Chemistry Principles and Surface Functionalization of Nanomaterials, Biomedical Applications of Functionalized Nanomaterials, Pelter et al., 1970; Ishihara et al., 2000, Encyclopedia of Materials: Science and Technology, Ring Systems with at least Two Fused Heterocyclic Five- or Six-membered Rings with no Bridgehead Heteroatom, Peptides: Synthesis, Structures, and Applications, Leona J. Rubin, ... William R. Sherman, in, Polymer Science: A Comprehensive Reference. The reaction happens slowly at room temperature (faster on gentle warming) without a great deal exciting to observe - unlike in the acyl chloride case where hydrogen chloride fumes are produced. Comparing acid anhydride with acyl chloride. The coupling of urethane-protected amino acids runs nearly without racemization. Decarboxylation reaction. Subsequent polymer modification of antibodies provides much higher radioactivity per molecule than if DTPA is directly coupled to the protein. The hydrogen is being replaced by an ethanoyl group, CH3CO-. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. written as: \[(CH_3CO)_2O + H_2O \longrightarrow 2CH_3COOH \]. Conjugation of antibody through DTPA crosslinks may be a major reason some immunoglobulins lose antigen-binding activity after modification (Lanteigne and Hnatowich, 1984). P.W. But beware!
The molecule below is 2-hydroxybenzoic acid (also known as 2-hydroxybenzenecarboxylic acid). Cyclic acid anhydride reactions with triorganoaluminum compounds account for most of the literature in this area. Except for inner anhydrides, the NCAs, and the inner anhydrides of aminodicarboxylic acids (Bergmann and Zervas, 1932), anhydrides of amino acids or peptides had not been prepared and applied in peptide syntheses before 1950. Upon nucleophilic attack, the anhydride yields one carboxylic acid for every acylated product. The reasons for using ethanoic anhydride rather than ethanoyl chloride include: Ethanoic anhydride is cheaper than ethanoyl chloride. You can say that the phenol has been acylated or has undergone acylation. These reactions are just the same as the corresponding acyl chloride reactions except: Modifying the general equation we've just looked at, you will see that you just get two molecules of ethanoic acid produced. DTPA reacts with amine-containing molecules via ring opening of its anhydride groups to create amide bond linkages.
DTPA also can be used to modify amine-containing polymers, such as poly-l-lysine, to create a chelating polymer possessing multiple metal binding sites (Trubetskoy et al., 1993). During the reactions of ethanoic anhydride, the red part behave just like chlorine atom of acyl chloride, it is always intact and replace just like chlorine atom.
The reactions of acid anhydrides are rather like those of acyl chlorides except that during their reactions, a molecule of carboxylic acid is produced rather than the HCl formed when an acyl chloride reacts.
Metal-chelate bonds are created through dative interactions with the unshared pair of electrons on each oxygen and nitrogen atom on DTPA, thus creating the potential for eight coordination sites with metal ions (from three nitrogens and five oxygens). Using thionyl chloride (SOCl,) instead of phosgene gives lower yields: A convenient synthesis of symmetrical anhydrides has been found in the reaction of carbodiimides with protected amino acids more than 10 years earlier by Muramatsu and Hagitani (1959). Symmetric anhydrides are the acylating agents in the “activating reagent mode” of carbodiimide coupling.
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