Glutaraldehyde condensation

A disadvantage of the glutaraldehyde condensation method is that dimers of the hapten and polymers of carrier protein may also form. To overcome this problem, the reaction time is limited to 2-3 h, or an excess of an amine-containing compound, e.g., lysine or cysteamine hydrochloride, is added. A two-step approach also minimizes dimerization. ... 

Reactions with dialdehydes allow the introduction of two additional rings in one step. Thus, condensation of 1 -(2-aminoethyl)pyrrole with glutaraldehyde and benzotriazole gives tricyclic intermediate 627 in which the benzotriazolyl moiety can be readily substituted with nucleophiles to give products 628 (Scheme 97) <2002JOC8220>. Condensation of ethyl ester of L-tryptophan with 2,5-dimethoxytetrahydrofuran and benzotriazole in acetic acid gives tetracyclic intermediate 629 which upon treatment with nucleophiles (silyl derivatives) is converted to products 630 <1999T3489>. 

Pseudopelletierine has been obtained from the bark of the pomegranate tree (Punica granatum L.).2-5 The synthesis of the alkaloid from glutaraldehyde, methylamine, and calcium acetonedicarboxylate was first achieved by Menzies and Robinson.6 The synthetic method subsequently was improved by Schopf and Lehmann,7 and others.8 9 The condensation of a dialdehyde with an amine and acetonedicar-boxylic acid to form a heterobicyclic compound (an alkaloid or alkaloid analog, usually employing mild or so-called physiological conditions) is sometimes referred to as a Robinson-Schopf synthesis. 

Fig. 19. Schiff base condensation of glutaraldehyde with enzyme amino...

Condensation reactions of aniline and of other bases with aromatic aldehydes to give Schiff s bases are accelerated by ultraviolet light in buffered media. For example, o-phenylenediamine reacts with formic acid to yield benzimidazole and acetylacetone reacts with guanidine to form 2-amino-4,6-dimethylpyrimidine.162 Similarly, lobelanine is formed by the photocondensation of glutaraldehyde, benzoylacetic acid, and methylamine hydrochloride.163... 

T Tashima, M Imai, YY Kuroda, S Yagi, T Nakagawa. Structure of a new oligomer of glutaraldehyde produced by aldol condensation reaction. J Org Chem 56 694-697, 1991. 

Peptide amide bond cleavage, A-atkylation of the amide bonds, imidoester reaction Carbamylation and thiocarbamylation method, diazotization, the four-component condensation reaction, glutaraldehyde treatment... 

The classical synthesis of pseudopelletierine by R. Robinson (1924), as improved by later work of C. Schdpf (1935), K. Ziegler (1950), and A. C. Cope (1951), involves condensation of glutaraldehyde with methylamine and acetonedicarboxylic... 

The preparation described here is an improvement of the previous procedure. The double condensation of glutaraldehyde with the amino group of (R)-(-)-phenylglycinol (related to the Robinson-Schopf condensation) probably leads to the expected product via the formation of an intermediate of type and/or B. 

A biological equivalent of a Pictet-Spengler reaction has been proposed to account for the formation of tangutorine, a racemic alkaloid isolated from a Nitraria species. Alkaloids in this species appear to be derived from lysine and a dimeric condensation product of glutaraldehyde is a biomimetic analog. When this material was synthesized and allowed to react with tryptamine, a tangutorine structure was obtained and was converted to material identical to the natural product [362]. 

Condensation of glutaraldehyde with urea is reported to afford 4,8-dihydroxy-3,4,5,6,7,8-hexa-hydro-l,3-diazocin-2(l/f)-one (36) (Equation (12)) <84USP4454133>. Dialkylation of thiourea with 1,5-dibromopentane affords 2-thione (14) in ca. 40- % yield (Equation (13)) <83MI 922-04>. 

Formaldehyde, glyoxal, glutaraldehyde, polyaldehyde (polyacrolein), aldehyde-amine condensation products, aldehyde-glycol condensation products, bronopol o-Phenyl phenol, o-benzyl-jn-chlorophenol,p-chloro-m-xylenol, o, p, p -trichloro-o -hydroxydiphenyl ether (Triclosan) Nonylphenoxypoly(ethyleneoxy) ethanol-iodine complex, ethoxylated nonyl phenol-iodine complex, polyvinyl pyrrolidone-iodine complex... 

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