Hydrolysis of allantoate

The rates of hydrolysis and racemization of allantoin (5-ureidohydantoin) were measured as a function of pH and temperature. Both reactions are susceptible to acid and base catalysis. Spontaneous hydrolysis of the neutral and anionic forms of allantoin determines the ratepH profile at pH values from 2 to 13.Allantoin is converted to allantoate (diureidoacetate) which is transformed to glyoxylate and urea in acid media. At pH values N 3 ammonia is formed directly from the ureido grouping of allantoin.The rates of racemization of (-)-allantoin and of L( -)-and D(+)-hydantoin-5-acetic acid were compared. Both reactions involved most probably enolization of the -CH-C=O moiety of the hydantoin rings.

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Hydrolysis and racemization of allantoin

Vogels

Windt

Bassie

1969

Recl. Trav. Chim. Pays‐Bas

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Cyanate decomposition catalyzed by certain bivalent anions

Vogels

Uffink

Drift

1970

Recl. Trav. Chim. Pays‐Bas

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Ammonia production from cyanate was measured as a function of p H . The kinetic description of the process included acid-catalyzed hydrolysis of isocyanic acid and spontaneous hydrolysis of isocyanic acid and cyanate. These reactions were predominant at pH values below 2, between 3 and 8, and above 9 , respectively.The hydrolysis was strongly catalyzed by certain bivalent anions. The geometry of the anion appeared to be an important factor in the catalytic process, since carbonate, phosphate, succinate, maleate, citrate and phthalate were catalysts, whereas other bivalent anions, viz. sulfate, oxalate, fumarate and isophthalate, were without effect. Catalysis by bivalent anions was supposed to proceed via carbamoyl derivatives of the anions. The negatively charged group of the carbamoyl derivative was thought to cause an intramolecular general basecatalyzed react ion.The implications of this study for the mechanism of urcase action were considered. IntroductionCyanate is a product of non-enzymic hydrolysis of urea 1 and carbamoyl derivatives e.g. allantoate (diureidoacetate), N-carbamoylglycine (hydantoate) and carbamoyl phosphate 2 , 3 . Its formation during the enzymic hydrolysis of urea by urease 4-6 and allantoate by allantoate amidohydrolase 7,*, is questionable.This communication deals with the stability of cyanate as a function of pH and special attention is given to the catalytic effect of certain bivalent anions.

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Ureolytic nitrification at low pH by Nitrosospira spec.

Boer¹,

Laanbroek²

1989

Arch. Microbiol.

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Hydrolysis of allantoate

Cited by 16 publications

References 5 publications

Hydrolysis and racemization of allantoin

Hydrolysis and racemization of allantoin

Cyanate decomposition catalyzed by certain bivalent anions

Ureolytic nitrification at low pH by Nitrosospira spec.

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