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Behavior of fluorinated analogs of L-(3,4-dihydroxyphenyl)alanine and L-threo-(3,4-dihydroxyphenyl)serine as substrates for Dopa decarboxylase.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Voltattorni, Carla Borri Bertoldi, Mariarita Bianconi, Silvia Deng, Wei-Ping Wong, Kelli A. Kim, Inho Herbert, Brian K. Kirk, Kenneth L. |
| Copyright Year | 2002 |
| Abstract | We have determined the kinetic parameters for Dopa decarboxylase (DDC) of three ring-fluorinated analogs of 3,4-dihydroxyphenylalanine (Dopa). The rank order of catalytic efficiency of decarboxylation (k(cat)/K(m)) is Dopa>6-F-Dopa>2-F-Dopa>5-F-Dopa. This rank is consistent with previous in vivo and in vitro studies which indicate that, of the fluorinated analogs, 6-F-Dopa has pharmacokinetics that are most suited for positron emission tomographic (PET) evaluation of dopamine function. The effectiveness of PET as a diagnostic tool, the convenient half-life of (18)F (110 min) and the favorable pharmacokinetics of 6-[(18)F]FDOPA have combined to make this an extremely valuable reagent to study dopaminergic activity. The reactions of the related fluorinated DOPS analogs show that, while 6-F-threo-3,4-(dihydroxyphenyl)serine (DOPS) is decarboxylated at approximately the same rate as the non-fluorinated substrate, 2-F-threo-DOPS is not converted into the corresponding amine. In both cases a Pictet-Spengler condensation with the pyridoxal 5(')-phosphate (PLP) cofactor occurs to produce tetrahydroisoquinolines. Condensation of fluorinated catecholamines and catechol amino acids with endogenous aldehydes will be investigated as an approach to study possible mechanisms of L-Dopa-linked neurotoxicity. |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/S0006-291X(02)00643-5 |
| PubMed reference number | 12083775 |
| Journal | Medline |
| Volume Number | 295 |
| Issue Number | 1 |
| Alternate Webpage(s) | http://www.dsnm.univr.it/documenti/Persona/curr/curr882207.pdf |
| Alternate Webpage(s) | http://www.dnbm.univr.it/documenti/Persona/curr/curr916468.pdf |
| Alternate Webpage(s) | http://www.dnbm.univr.it/documenti/Persona/curr/curr862259.pdf |
| Alternate Webpage(s) | https://doi.org/10.1016/S0006-291X%2802%2900643-5 |
| Journal | Biochemical and biophysical research communications |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
