The mechanism of the transamination reaction

Snell, Esmond E.; Jenkins, W. Terry

doi:10.1002/jcp.1030540413

Cited by 69 publications

(36 citation statements)

References 33 publications

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“…The general theory of the mechanism of action of enzymes using pyridoxal 5'-phosphate as a coenzyme has been put forward by Braunstein et al (1,2) and by Snell and co-workers (3)(4)(5). It involves reaction of the aldehyde function and the amino group of an amino acid to form a Schiff base.…”

Section: Rmentioning

confidence: 99%

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Lapper¹,

Mantsch²,

Smith³

1975

Can. J. Chem.

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SMITH. Can. J. Chem. 53,2406 (1975. The 13C chemical shifts and 13C-31P spin-spin couplings (where applicable) are reported for pyridoxine, pyridoxamine, pyridoxal, pyridoxamine phosphate, and pyridoxal phosphate. Resonance assignments are made by consideration of substituent chemical shift effects, as tested on an analogous series of pyridine derivatives. Increased shielding of the C4' and C5' methylene groups of the vitamin B6 compounds and the methyl groups of 3,4-dimethylpyridine relative to the predicted values are attributed to steric compression. In aqueous solution pyridoxal exists as the hemiacetal form, although at high p H it is in rapid equilibrium with a significant amount of the aldehyde form. Pyridoxal phosphate exists as the aldehyde at high pH, as the hydrated aldehyde at low pH, and in a slow equilibrium between detectable amounts of both species at p H 4. The 13C-31P couplings through two bonds lie in the range 4.5 f 0.5 Hz found for a variety of other organic phosphates. The couplings through three bonds indicate a preference for a trans arrangement of the phosphorus and ring carbon-5. ROY D. LAPPER, HENRY H. MANTSCH et IAN C. P. SMITH. Can. J. Chem. 53,2406Chem. 53, (1975. On a mesurC les dkplacements chimiques du 13C et les constantes de couplage spin-spin entre13C et 31P (dans les phosphates) pour la pyridoxine, pyridoxamine, pyridoxal, phosphate de pyridoxamine et phosphate de pyridoxal. Les attributions sont faites en considCrant les effets des substituants sur le dkplacement chimique dans une skrie analogue des pyridines substitukes. L'accroissement du blindage des carbones mkthylCniques 4' et 5' des composCs de la vitamine B6 et des groupes mCthyles du dirnkthyl-3,4 pyridine par rapport aux valeurs calculks, est attribuC a une compression stkrique. En solution aqueuse le pyridoxal existe sous la forme hemiacktale bien qu'a p H ClevC I'hCmiacktale soit en Cquilibre rapide avec une quantitC importante d'aldehyde. A p H ClevC, le phosphate de pyridoxal existe sous la forme aldkhyde, a p H faible sous forme aldehyde hydratk, et a p H 4 on a un Cquilibre lent entre des quantitts dicelables des deux espkes. Les constantes de couplage de 13C-31P a travers deux liaisons, se situent aux alentours de 4.5 + 0.5 Hz. Cette valeur correspond aux valeurs trouvCes pour divers phosphates organiques. Les couplages a travers trois liaisons suggtrent une forte prefkrence pour un arrangement trans du phosphore par rapport au carbone-5 du cycle.[Traduit par le journal] Introduction The vitamin B, group of compounds consists of pyridoxine, pyridoxamine, and pyridoxa 1 and their phosphates.5 Of these various forms the most active and effective over a large range of organisms appears to be pyridoxal 5'-phosphate, also known as codecarboxylase or cotransaminase. This compound represents the co-

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Section: Rmentioning

confidence: 99%

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Lapper¹,

Mantsch²,

Smith³

1975

Can. J. Chem.

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“…The structural requirements for catalysis of the decarboxylation reaction thus resemble those found for the transamination reaction (Ikawa and Snell, 1954b;Snell and Jenkins, 1959).…”

Section: Table I1mentioning

confidence: 74%

Pyridoxal-Catalyzed Decarboxylation of Amino Acids^*

Kalyankar¹,

Snell²

1962

Biochemistry

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“…Although molecule QDI was reported more than a century ago [12], its reactivity has been poorly investigated so far. Transamination reaction -well known reaction in biochemistry accomplished by transaminases [13,14] -has been recently investigated on QDI. Using primary alkylamines, this approach appeared to be an efficient and green method to reach N-substituted QDI (QDI-R 4 , Scheme 1) [15].…”

Section: Versatile Transamination In Quinonediimine Chemistrymentioning

confidence: 99%

Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores

Chen

Bert

Pascal

et al. 2019

Tetrahedron Letters

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Transamination reactions occurring on 2,5-diaminobenzoquinonediimine (QDI) in presence of ethylenediamine yields fluorescent 1,2,3,4-tetrahydropyrazino[2,3-g]quinoxaline (1). When the same reaction is carried out with N,N'-bis(aminoethyl)-1,3propanediamine, a novel cationic quinoxalinium species (2) is isolated, which can be further condensed to a benzaldehyde derivative to afford a benzimidazolo-fused quinoxaline dye (3) that is a water-soluble fluorophore in the UV-visible range.

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The mechanism of the transamination reaction

Cited by 69 publications

References 33 publications

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Pyridoxal-Catalyzed Decarboxylation of Amino Acids^*

Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores

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The mechanism of the transamination reaction

Cited by 69 publications

References 33 publications

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Carbon-13 Nuclear Magnetic Resonance Studies of Compounds of the Vitamin B6 Group and Related Pyridine Derivatives

Pyridoxal-Catalyzed Decarboxylation of Amino Acids*

Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores

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Pyridoxal-Catalyzed Decarboxylation of Amino Acids^*