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Abenzyl 10-formyl-trideazafolic acid (abenzyl 10-formyl-TDAF): an effective inhibitor of glycinamide ribonucleotide transformylase

Academic Article
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Overview

related to degree

  • Haynes, Nancy-Ellen, Ph.D. in Organic Chemistry, Scripps Research 1991 - 1996

authors

  • Boger, Dale
  • Haynes, Nancy-Ellen
  • Warren, M. S.
  • Ramcharan, J.
  • Marolewski, A. E.
  • Kitos, P. A.
  • Benkovic, S. J.

publication date

  • September 1997

journal

  • Bioorganic & Medicinal Chemistry  Journal

abstract

  • The synthesis of N-[7-(2-amino-3,4-dihydro-4-oxo-quinazolin-6-yl) -6-formyl-1-oxo-heptyl]-L-glutamic acid (2, abenzyl 10-formyl-5,8,10-trideazafolic acid) as a potential enzyme-assembled tight binding inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) or aminoimidazole carboxamide ribonucleotide transformylase (AICAR Tfase) is reported. The inhibitor was prepared by a convergent synthesis utilizing the sequential alkylations of acetaldehyde dimethylhydrazone with 6 and 8. The agent exhibited effective inhibition of GAR Tfase (Ki = 4.5 +/- 0.3 microM) and more modest inhibition of AICAR Tfase (Ki = 42 +/- 11 microM).

subject areas

  • Cell Division
  • Enzyme Inhibitors
  • Glutamates
  • Humans
  • Hydroxymethyl and Formyl Transferases
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phosphoribosylglycinamide Formyltransferase
  • Quinazolines
  • Spectrometry, Mass, Fast Atom Bombardment
  • Tumor Cells, Cultured
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/s0968-0896(97)00123-5

PubMed ID

  • 9354240
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Additional Document Info

start page

  • 1847

end page

  • 1852

volume

  • 5

issue

  • 9

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