Literature DB >> 4505665

5-Fluoro-2'-deoxyuridylate: covalent complex with thymidylate synthetase.

D V Santi, C S McHenry.   

Abstract

5-Fluoro-2'-deoxyuridylate causes a rapid inactivation of thymidylate synthetase that is dependent upon prior complexation of the cofactor 5,10-methylenetetrahydrofolate. The enzyme-5-fluoro-2'-deoxyuridylate complex may be isolated on nitrocellulose membranes and is not disrupted by 6 M urea. Upon reaction of 5-fluoro-2'-deoxyuridylate with the enzyme in the presence of 5,10-methylenetetrahydrofolate a rapid loss of absorbance is observed at 269 nm, the absorption maximum for the pyrimidine chromophore. It is concluded that a covalent bond is formed between the 6-position of 5-fluoro-2'-deoxyuridylate and a nucleophilic group of the enzyme that is involved in catalysis.

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Year:  1972        PMID： 4505665      PMCID： PMC426818          DOI： 10.1073/pnas.69.7.1855

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  15 in total

1.  Fluorinated pyrimidines. XXVI. Mammalian thymidylate synthetase: its mechanism of action and inhibition by fluorinated nucleotides.

Authors:  P Reyes; C Heidelberger
Journal:  Mol Pharmacol       Date:  1965-07       Impact factor: 4.436

2.  Properties of thymidylate synthetase from dichloromethotrexate-resistant Lactobacillus casei.

Authors:  T C Crusberg; R Leary; R L Kisliuk
Journal:  J Biol Chem       Date:  1970-10-25       Impact factor: 5.157

3.  Model studies of thymidylate synthetase. Neighboring-group facilitation of electrophilic substitution reactions of uracil furanosides.

Authors:  D V Santi; C F Brewer
Journal:  J Am Chem Soc       Date:  1968-10-23       Impact factor: 15.419

4.  Small-scale preparation of 5'-nucleotides and analogs by carrot phosphotransferase.

Authors:  C L Harvey; E M Clericuzio; A L Nussbaum
Journal:  Anal Biochem       Date:  1970-08       Impact factor: 3.365

5.  An exchange between the hydrogen atom on carbon 5 of deoxyuridylate and water catalyzed by thymidylate synthetase.

Authors:  M I Lomax; G R Greenberg
Journal:  J Biol Chem       Date:  1967-03-25       Impact factor: 5.157

6.  On the properties and utility of a membrane filter assay in the study of isoleucyl-tRNA synthetase.

Authors:  M Yarus; P Berg
Journal:  Anal Biochem       Date:  1970-06       Impact factor: 3.365

7.  The mechanism of the condensation of formaldehyde with tetrahydrofolic acid.

Authors:  R G Kallen; W P Jencks
Journal:  J Biol Chem       Date:  1966-12-25       Impact factor: 5.157

8.  Nucleosides XXXVI. Transformation of arabinopyrimidine nucleosides.

Authors:  J J Fox; N C Miller; R J Cushley
Journal:  Tetrahedron Lett       Date:  1966-10       Impact factor: 2.415

9.  Nucleosides. 58. Transformations of pyrimidine nucleosides in alkaline media. 3. The conversion of 5-halogenouridines into imidazoline and barbituric acid nucleosides.

Authors:  B A Otter; E A Falco; J J Fox
Journal:  J Org Chem       Date:  1969-05       Impact factor: 4.354

10.  Tetrahydrofolate-dependent labilization of the hydrogen atom on carbon 5 of 5'-deoxycytidylate, a step in the deoxycytidylate hydroxymethylase reaction.

Authors:  Y C Yeh; G R Greenberg
Journal:  J Biol Chem       Date:  1967-03-25       Impact factor: 5.157
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  46 in total

1.  A specific increase in chloroplast gene mutations following growth of Chlamydomonas in 5-fluorodeoxyuridine.

Authors:  E A Wurtz; B B Sears; D K Rabert; H S Shepherd; N W Gillham; J E Boynton
Journal:  Mol Gen Genet       Date:  1979-03-05

2.  The teratogenic effects of 5-fluoro-2-desoxyuridine (F.U.D.R.) on the Wistar rat fetus with particular reference to cleft palate.

Authors:  M W Ferguson
Journal:  J Anat       Date:  1978-05       Impact factor: 2.610

Review 3.  TAS-102, a novel antitumor agent: a review of the mechanism of action.

Authors:  Heinz-Josef Lenz; Sebastian Stintzing; Fotios Loupakis
Journal:  Cancer Treat Rev       Date:  2015-06-06       Impact factor: 12.111

4.  Reexamining a proposal: thymidylate synthase 5'-untranslated region as a regulator of translation efficiency.

Authors:  Soma Ghosh; Jordan M Winter; Kalpesh Patel; Scott E Kern
Journal:  Cancer Biol Ther       Date:  2011-10-15       Impact factor: 4.742

5.  Perturbation of chloroplast gene transmission in diploid and triploid zygotes of Chlamydomonas reinhardi by 5-fluorodeoxyuridine.

Authors:  R F Matagne; M C Beckers
Journal:  Curr Genet       Date:  1983-09       Impact factor: 3.886

Review 6.  Pyrimidine metabolism in schistosomes: A comparison with other parasites and the search for potential chemotherapeutic targets.

Authors:  Mahmoud H El Kouni
Journal:  Comp Biochem Physiol B Biochem Mol Biol       Date:  2017-07-21       Impact factor: 2.231

7.  Thymidylate synthetase purified to homogeneity from human leukemic cells.

Authors:  A Lockshin; R G Moran; P V Danenberg
Journal:  Proc Natl Acad Sci U S A       Date:  1979-02       Impact factor: 11.205

8.  Pyrimidine metabolism in Tritrichomonas foetus.

Authors:  C C Wang; R Verham; S F Tzeng; S Aldritt; H W Cheng
Journal:  Proc Natl Acad Sci U S A       Date:  1983-05       Impact factor: 11.205

9.  A 19F nuclear magnetic resonance study of uptake and metabolism of 5-fluorocytosine in susceptible and resistant strains of Candida albicans.

Authors:  M Di Vito; F Podo; A Torosantucci; G Carpinelli; W L Whelan; D Kerridge; A Cassone
Journal:  Antimicrob Agents Chemother       Date:  1986-02       Impact factor: 5.191

10.  An evolutionary analysis of lateral gene transfer in thymidylate synthase enzymes.

Authors:  Adi Stern; Itay Mayrose; Osnat Penn; Shaul Shaul; Uri Gophna; Tal Pupko
Journal:  Syst Biol       Date:  2010-01-15       Impact factor: 15.683
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