1996
DOI: 10.1021/ja9527885
|View full text |Cite
|
Sign up to set email alerts
|

Mechanisms of Inactivation of γ-Aminobutyric Acid Aminotransferase by 4-Amino-5-fluoro-5-hexenoic Acid

Abstract: An investigation of the mechanisms of inactivation of the pyridoxal 5‘-phosphate (PLP)-dependent pig brain γ-aminobutyric acid (GABA) aminotransferase by 4-amino-5-fluoro-5-hexenoic acid (2), a monofluorinated analogue of the anticonvulsant drug vigabatrin, is described. Inactivation of [3H]PLP-reconstituted GABA aminotransferase with 2 followed by denaturation released the coenzyme in two forms, one as PLP and the other in a modified form in the ratio 7:3. All enzyme activity was lost upon inactivation by 2, … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

0
43
0

Year Published

2004
2004
2020
2020

Publication Types

Select...
8
1

Relationship

0
9

Authors

Journals

citations
Cited by 31 publications
(43 citation statements)
references
References 26 publications
0
43
0
Order By: Relevance
“…Given the great interest in fluorinated alkene functionality in chemical biology, for example, as latent triggers for enzyme inactivation, 30,32c,32d,39a as masked aldehyde 32a or carboxylate 32b equivalents, or as peptide bond isosteres, 40 there has been a significant effort in methodology development in this area. Approaches to monofluorovinyl group installation most commonly are formal nucleophilic fluoromethylenations, whereby a EWG-CY(-)-F reagent is condensed with a carbonyl center.…”
Section: Resultsmentioning
confidence: 99%
“…Given the great interest in fluorinated alkene functionality in chemical biology, for example, as latent triggers for enzyme inactivation, 30,32c,32d,39a as masked aldehyde 32a or carboxylate 32b equivalents, or as peptide bond isosteres, 40 there has been a significant effort in methodology development in this area. Approaches to monofluorovinyl group installation most commonly are formal nucleophilic fluoromethylenations, whereby a EWG-CY(-)-F reagent is condensed with a carbonyl center.…”
Section: Resultsmentioning
confidence: 99%
“…The synthesis of 3-fluorovinylglycine (18) was reported by Thornberry et al 13 (Scheme 3). The monofluorovinyl group from starting material 2-fluoroacrolein (15) has been transferred in the reaction with 4,4'-dimethoxybenzhydrylamine (16) into the desired product.…”
Section: Scheme 1 Multi-step Synthesis Of (E)-β-(fluoromethylene)-m-tyrosine (7)mentioning
confidence: 99%
“…29,30 To the best of our knowledge, there is one notable exception. 72,73 A clever solution to this problem has been reported by Leo´n, Sua´rez and coworkers by using a reductive b-elimination of 1,1-dihalo alditols 31 promoted by chromium(II) chloride (Scheme 22). 74 The method is limited to gem-dihalo compounds, the latter are accessible in two steps from carbohydrates.…”
Section: Hx Eliminationmentioning
confidence: 99%