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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Phillips, Robert S. |
| Description | Author Affiliation: Phillips RS ( Department of Chemistry, University of Georgia, Athens, GA 30602, USA) |
| Abstract | Pyridoxal-5′-phosphate (PLP) is a versatile cofactor that enzymes use to catalyze a wide variety of reactions of amino acids, including transamination, decarboxylation, racemization, β- and γ-eliminations and substitutions, retro-aldol and Claisen reactions. These reactions depend on the ability of PLP to stabilize, to a varying degree, α-carbanionic intermediates. Furthermore, oxidative decarboxylations and rearrangements suggest that PLP can stabilize radical intermediates as well. The reaction mechanisms of two PLP-dependent enzymes are discussed, kynureninase and tyrosine phenol-lyase (TPL). Kynureninase catalyzes a retro-Claisen reaction of kynurenine to give anthranilate and alanine. The key step, hydration of the γ-carbonyl, is assisted by acid–base catalysis with the phosphate of the PLP, mediated by a conserved tyrosine, and an oxyanion hole. TPL catalyzes the reversible elimination of phenol, a poor leaving group, from l -tyrosine. In TPL, the C $_{β}$ –C $_{γ}$ bond cleavage is accelerated by ground state strain from the bending of the substrate ring out of the plane with the C $_{β}$ –C $_{γ}$ bond. This article is part of a Special Issue entitled: Cofactor-dependent proteins: evolution, chemical diversity and bio-applications. |
| ISSN | 00063002 |
| Journal | Biochimica et Biophysica Acta (BBA) - Reviews on Cancer |
| Issue Number | 9 |
| Volume Number | 1854 |
| Language | English |
| Publisher | Elsevier |
| Publisher Date | 2015-09-01 |
| Publisher Place | Netherlands |
| Access Restriction | Open |
| Subject Keyword | Hydrolases Chemistry Pyridoxal Phosphate Physiology Tyrosine Phenol-Lyase Catalysis Research Support, N.I.H., Extramural Biochemistry |
| Content Type | Text |
| Resource Type | Article |
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