A- succinimide

Under basic coupling conditions an aspartyl peptide that has a /3-phenacyl ester i converted to a succinimide. The use of PhSeH prevents the a,/3-rearrangement c the aspartyl residue during deprotection. 

When caring for a patient taking a succinimide for absent seizures, the nurse monitors the patient for blood dyscrasias. Which of the following symptoms would indicate that the patient may be developing a blood dyscrasia ... 

A. Succinimide silver salt (Note 1). A 3-1., two-necked, round-bottomed flask equipped with a mechanical stirrer and a pressureequalizing dropping funnel is charged with a solution of 28.9 g. (0.292 mole) of succinimide (Note 2) in 1.2 1. of absolute ethanol (Note 3). A solution of 48.58 g. (0.286 mole) of silver nitrate in 200 ml. of dimethyl sulfoxide (Note 4) is added in one portion. The resulting solution is stirred as 700 ml. (0.280 mole) of 0.4 M... 

Isocyanates can be replaced with a phthalimide and a succinimide to give hemiaminals 122 and 123 in 68% and 65% yield, respectively (Scheme 53).185... 

These results can be rationalized as follows. Cyclic imide formation is maximal with a Gly residue because of its minimal steric interference. In contrast, steric bulk (i.e., size and branching) of the C-flanking residue is the major factor decreasing the reactivity of Asn to form a succinimide. Residues with a functionalized side chain, namely serine, threonine, and histidine, behaved as exceptions to this rule (see above). 

The discovery of the sedative/hynoptic activity of derivatives of barbituric acid has led to very extensive dissections of that molecule. One outcome of this work is the realization that acylurea and acylamide derivatives often exhibit CNS depressant activity. A fair number of such molecules have been prepared that contain a succinimide or glutarimide pharmacophore. For example, Michael addition of cyanide to the stereochemically xmdefined cinnamate... 

Another method for the preparation of bicyclic lactams consists of formation of a succinimide 5, followed by reaction with a hydride or an organometallic reagent to give a carbonyl equivalent that is readily cyclized upon workup10 15. 

Regioselective reduction of a succinimide intermediate for a (-i-)-heliotridine synthesis [269] must be due to the influence of the acetoxy group. It is conjectured that the a-a array of the intervening carbon atoms activates the carbonyl. Steric effects should he minimal on the choice of the two sites. 

In a number of reactions that are written as dissociative electron attachments, short-lived radical anions are in fact intermediates. A case in point is 5BrUra (Chap. 10). An interesting behavior is shown by the radical anion of N-bromo-succinimide which does not release a bromide ion but rather fragments into a bromine atom and a succinimide anion [reactions (17) and (18)] (Lind et al. 1991). 

Isomerization of aspartyl-X residues can occur via a succinimide intermediate (Fig. 132). The isomerized aspartyl residue can be detected by peptide mapping, Edman sequencing, and selective methylation of the iso-Asp peptide using carboxyl methyl transferase enzyme. Succinimide sites... 

Detergent-dispersant interactions at surfaces. In 4-ball wear tests, an ashless dispersant was found to have an adverse effect on ZDDP-sulfonate-carbonate hardcore RM additives. A high molecular weight Schiff base had the worst effect, followed by a bis-PIBS m-PIBS had the least adverse effect. Interactions among additives affects valve train wear. One of the effects is that a succinimide together with other additives increases the decomposition temperature of ZDDP (Ramakamur, 1994 Shirahama and Hirata, 1989). 

Micellar solutions of detergents such a sulfonates, phenolates and salicylates enhance the solubilizing properties of succinimide additives. For small concentrations of about 0.25% w/w sulfonate and 2.8% succinimide, a synergistic effect is observed, but for high sulfonate concentrations, the quantity of acid solubilized is less than that observed for succinimide alone (Bradley and Jaycock, 1972). A different mechanism exists for the solubilization of those weak acids and for strong acids. The different interaction between the amine groups in the polar head of a succinimide micelle and a weak acid (WH), and for a strong acid (SH), indicates that the weak acid is much better solubilized as ... 

The first compound of the fulgide family developed by Heller et al was a succinimide which was called a fulgimide. The general formula is shown in compound 5. 

Scheme 24 Absolute asymmetric photocyclization of a succinimide derivative involving a 1,5-hydrogen shift.

The effect of the incorporation of a succinimide (21) moiety into a peptide chain (another type of Cj -o- Nj. ring restriction) has been examined carefully (60, 61). The five-membered succinimide annular system is an intermediate in the repair of selective degradations of side-chain deamidated proteins. It has been shown both theoretically and experimentally that L-Asu-Xxx- (Asu, a-aminosuccinyl) dipeptide sequences strongly favor the type-lT fS-tum, a behavior similar to that of the y-lactam modification discussed above. 

Labeling antibodies by covalent coupling of a biotinyl group is simple and normally does not have any adverse effect on the antibody (6). Most biotinylations are performed using a succinimide ester of biotin. The reagent reacts with primary amines of the lysine residues or the amino terminus on the antibody to form amide bonds. The protocol described below (7,8) uses a water-soluble analog of A -hydroxylsuccinimide biotin (Pierce Co., Rockford, IL), which can be dissolved directly in the reaction buffer. Biotin-coupled antibodies are stable under normal storage conditions. 

Metabolites 22-38 with chlorine and a succinimide moiety are rare in nature. Based on the SAR results, it appears that several structural features of haterumaimides, such as the presence of hydroxyl groups at C6, C7, C12 and Cl8, a chlorine atom at C2 and an imido NH in ring C, are very important for the cytotoxicity. The hydrophilic OH and (CO)2NH groups in haterumaimides might increase cell membrane permeability to the molecules and/or enhance the stereo-electronic interaction between the molecules and a target molecule. 

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