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Computational studi...
Computational studies on Schiff-base formation : Implications for the catalytic mechanism of porphobilinogen synthase
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- Erdtman, Edvin (author)
- Högskolan i Borås,Örebro universitet,Akademin för naturvetenskap och teknik,Biofysikalisk kemi,Örebro universitet, Akademin för naturvetenskap och teknik,Institutionen Ingenjörshögskolan
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- Bushnell, Eric A. C. (author)
- Department of Chemistry and Biochemistry, University of Windsor, Windsor ON, Canada
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- Gauld, James W. (author)
- Department of Chemistry and Biochemistry, University of Windsor, Windsor ON, Canada
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- Eriksson, Leif A. (author)
- School of Chemistry, National University of Ireland (NUI Galway), Galway, Ireland
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(creator_code:org_t)
- Amsterdam : Elsevier, 2011
- 2011
- English.
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In: Computational and Theoretical Chemistry. - Amsterdam : Elsevier. - 2210-271X .- 2210-2728. ; 963:2-3, s. 479-489
- Related links:
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https://doi.org/10.1...
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Abstract
Subject headings
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- Schiff bases are common and important intermediates in many bioenzymatic systems. The mechanism by which they are formed, however,is dependent on the solvent, pH and other factors. In the present study we have used density functional theory methods in combination with appropriate chemical models to get a better understanding of the inherent chemistry of the formation of two Schiff bases that have been proposed to be involved in the catalytic mechanism of porphobilinogensynthase (PBGS), a key enzyme in the biosynthesis of porphyrins. More specifically, we have investigated the uncatalysed reaction of its substrate 5-aminolevulinic acid (5-ALA) with a lysine residue for theformation of the P-site Schiff base, and as possibly catalysed by the second active site lysine, water or the 5-ALA itself. It is found that cooperatively both the second lysine and the amino group of the initial 5-ALA itself are capable of reducing the rate-limiting energy barrier to14.0 kcal mol-1. We therefore propose these to be likely routes involved in the P-site Schiff-base formation in PBGS.
Subject headings
- NATURVETENSKAP -- Kemi -- Fysikalisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Physical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Andra medicinska och farmaceutiska grundvetenskaper (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Other Basic Medicine (hsv//eng)
Keyword
- Schiff base
- 5-Aminolevulinic acid
- Porphobilinogen synthase
- Density functional theory
- Catalysis
- NATURAL SCIENCES
- NATURVETENSKAP
- Physical chemistry
- Fysikalisk kemi
- Biophysical chemistry
- Biofysikalisk kemi
- Theoretical chemistry
- Teoretisk kemi
- Biochemistry
- Biokemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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