Succinimides hydrolysis

They are formed by heating dibasic acids or their anhydrides with ammonia. The hydrogen atom of the NH group is acidic and can be replaced by a metal. Mild hydrolysis breaks the ring to give the half amide of the acid. See succinimide and phthalimide. 

Condensation of allyl isocyanate with succinimide affords the cyclic diacylurea 39. Acid hydrolysis leads to ring opening of the succinimide (40). Oxymercuration of the terminal olefin bond with mercuric acetate in methanol solution affords the diuretic meralluride (41). ... 

Formal oxidation of pyrrolidine to the succinimide stage affords a series of compounds used as anticonvulsant agents for treatment of seizures in petit mal epilepsy. Knoevnagel condensation of benzaldehyde with ethyl cyanoacetate affords the unsaturated ester, 9. Conjugate addition of cyanide ion leads to the di-nitrile ester (10). Hydrolysis in mineral acid affords the succinic acid (11), presumably by decarboxylation of the intermediate tricarboxyllie acid. Lactamization with methylamine gives phensuximide (12). ... 

In the following paragraphs, we examine bioactive cyclic imides substituted on the ring and/or on the N-atoms, and begin with N-substituted suc-cinimides. CP-93,393 (4.177, R=R =H) is a selective 5-HT, serotonin autoreceptor agonist developed for the treatment of anxiety and depression. In the rat, hydrolysis of the succinimide bond was observed for the parent drug as well as for metabolites hydroxylated on the succinimide ring (4.177, R=OH,... 

The most important degradation mechanism of asparagine and glutamine residues is formation of an intermediate succinimidyl peptide (6.63) without direct backbone cleavage (Fig. 6.29, Pathway e). The reaction, which occurs only in neutral and alkaline media, begins with a nucleophilic attack of the C-neighboring N-atom at the carbonyl C-atom of the Asn side chain (slow step). The succinimide ring epimerizes easily and opens by hydrolysis (fast step), as shown in Fig. 6.27, to yield the iso-aspartyl peptide (6.64) and the aspartyl peptide (6.65) in a ratio of 3 1. 

Indeed, the choice of a nitrogen compound to be used as carrier in such O-alkyl prodrugs is not restricted to benzamides. Other amides were examined, e.g., phthalimide, succinimide, and saccharin. Thus, the saccharin prodrug of estradiol (11.50, R = 17/J-estradiol) underwent rapid nonenzymatic hydrolysis in rat and human plasma [85]. Administration of the prodrug to rats led to an impressive fivefold increase in the oral bioavailability of estradiol, and it was approximately nine times more potent orally, based on the 50% effective dose. 

The spotting experiment must be finished within 1 h after preparing streptavidin/poly (NAM-co-NAS) mixed solutions. Because the reaction between the succinimide esters of poly(NAM-co-NAS) and the amino groups of SA molecules and hydrolysis of the succinimide esters of poly (NAM-co-NAS) proceed before printing on substrates in 384-well, 3-D NPH-SA is difficult to be made on Au-coated slide activated with succinimide esters. 

Figure 2. Notation for organic reactions used by Kekule in his 1858 paper for the hydrolysis of succinimide to succinamic acid.

Figure 13.11. Formation and hydrolysis of succinimides derived from aspartic acid. Table 13.20. Preparation of imides and related compounds.

The direct introduction of bromine into the allylic position of an alkene using ZV-bromosuccinimide is known as the Wohl-Ziegler reaction. Bromination is carried out in anhydrous reagents (to avoid hydrolysis of the bromoimide), usually boiling carbon tetrachloride or chloroform solution. The progress of the reaction can be followed by the fact that at first the dense N-bromosuccinimide is at the bottom of the flask and is gradually replaced by succinimide, which rises... 

Many kinds of enzymes with different substrate specificities are involved in hydantoin hydrolysis. Ogawa et al. [10] found two hydantoin-hydrolyzing enzymes in Blastobacter sp. A17p-4. These enzymes were purified to homogeneity and characterized (Table 1). One hydrolyzed dihydropyrimidines and 5-monosubstituted hydantoins to the corresponding AT-carbamoyl amino acids. Since the hydrolysis of 5-substituted hydantoins by this enzyme was D-stereo-specific, this enzyme was identified as D-hydantoinase, which is identical with dihydropyrimidinase. The other one preferably hydrolyzed cyclic imide compounds such as glutarimide and succinimide more than cyclic ureide compounds such as dihydrouracil and hydantoin. Because there have been no reports on enzymes which show same substrate specificity as this enzyme, it is considered to be a novel enzyme, which should be called imidase [10]. 

Figure 12 Relative TNP hydrolysis rate catalyzed by 11 (20 pM) and Triton X-100 (10 mM) as a function of the concentration of inhibitor in 10% (v/v) MeOH aqueous solution at 25°C and pH 9.2 (20 mMCHES buffer) with/ = 0.10 (NaN03) (a) for phthalimide, (b) for succinimide, (c) for NaSCN.

A Schmidt reaction performed on poly(acrylic acid) has been also proposed 2>. Better methods involve the hydrazinolysis of poly(N-vinyl-succinimide)3), the hydrolysis of poly(N-vinyl-tert-butylcarbamate)4) ... 

Poly(sodium aspartate-co-asparagine-co-succinimide), (II), was prepared by the author [3] by hydrolysis of polysuccinimide with ammonium and sodium hydroxides. A method for preparing branched polysuccinimide derivatives of the current investigation was also provided. 

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