By Alton Meister (Auth.)

ISBN-10: 0123955238

ISBN-13: 9780123955234

ISBN-10: 0323161472

ISBN-13: 9780323161473

Biochemistry of the amino acids

summary: Biochemistry of the amino acids

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Glutamine, which may be considered as an acyl derivative of ammonia, possesses an unprotonated nitrogen atom, which would be available for transfer reactions in which the un-ionized form of ammonia may also participate. Ammonia is not active in the synthesis of Dglucosamine-6-phosphate, a reaction which, in contrast to the other amide nitrogen reactions, does not require adenosine triphosphate. Virtually all of the reactions involving amide nitrogen transfer are inhibited by aza-L-serine or 6-diazo-5-oxo-L-norleucine.

Substitution of hydroxylamine for ammonia led to the formation of a hydroxamate; this observation and the fact that inorganic pyrophosphate is formed suggest an enzyme-bound acyl adenylate intermediate. The conversion of xanthylic acid to guanylic acid has also been shown to involve amide nitrogen transfer from glutamine, but in certain systems ammonia is active. Xanthylic acid + glutamine + A T P + H 2 0 -> guanylic acid + glutamate + adenosine 5'-phosphate 4- pyrophosphate £ . Glutamic Acid and Glutamine 625 A purified enzyme preparation obtained from pigeon liver was active with glutamine and ammonia, and when xanthylic acid labeled with O 1 8 in the 2-hydroxyl group was used, isotope appeared mainly in the phosphate group of adenosine 5'-phosphate (242-244).

S Ο <4Η ο C ω Κ υ CD £ . Glutamic Acid and Glutamine 633 The mechanism of glycinamide ribonucleotide synthesis became clear as a result of the discovery of 5 -phosphoribosyl-1 -pyrophosphate (see p. 615). The enzyme 5-phosphoribose pyrophosphokinase catalyzes the transfer of the pyrophosphate moiety of adenosine triphosphate to ribose 5-phosphate. 5-Phosphoribosyl-1-pyrophosphate reacts with glutamine to yield 5-phosphoribosylamine. This reaction, which is catalyzed by the enzyme 5-phosphoribosyl pyrophosphate amidotransferase, may be represented as follows (318, 319): 5-Phosphoribosyl-1 -pyrophosphate + glutamine + H 2 0 ->■ 5-phosphoribosylamine + pyrophosphate + glutamate The instability of 5-phosphoribosylamine has thus far prevented its isolation, but synthetic preparations of this compound obtained by reaction of ribose 5-phosphate with liquid ammonia were active when incubated with glycine and adenosine triphosphate in the enzymatic synthesis of glycinamide ribonucleotide.

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Biochemistry of the Amino Acids by Alton Meister (Auth.)

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