10-Formyl-5,8,10-trideazafolic acid (10-formyl-TDAF): a potent inhibitor of glycinamide ribonucleotide transformylase.

[1]  D. Boger,et al.  Functionalized analogues of 5,8,10-trideazafolate as potential inhibitors of GAR Tfase or AICAR Tfase. , 1997, Bioorganic & medicinal chemistry.

[2]  D. Boger,et al.  Abenzyl 10-formyl-trideazafolic acid (abenzyl 10-formyl-TDAF): an effective inhibitor of glycinamide ribonucleotide transformylase. , 1997, Bioorganic & medicinal chemistry.

[3]  D. Boger,et al.  Functionalized analogues of 5,8,10-trideazafolate: development of an enzyme-assembled tight binding inhibitor of GAR Tfase and a potential irreversible inhibitor of AICAR Tfase. , 1997, Bioorganic & medicinal chemistry.

[4]  E. Taylor,et al.  Synthesis of a pyrimido[4,5-b]azepine analog of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF) , 1997 .

[5]  C. Spanka,et al.  Synthesis of N-{4-[2-(2-Amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)- ethyl]benzoyl}-l-glutamic Acid: A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid† , 1996 .

[6]  S. B. Gates,et al.  Synthesis and biological evaluation of a new series of dihydrofolate reductase inhibitors based on the 4-(2,6-diamino-5-pyrimidinyl)alkyl-L-glutamic acid structure , 1996 .

[7]  G. P. Beardsley,et al.  The Human purH Gene Product, 5-Aminoimidazole-4-carboxamide Ribonucleotide Formyltransferase/IMP Cyclohydrolase , 1996, The Journal of Biological Chemistry.

[8]  C. Johnson,et al.  Analogues of 10-deazaaminopterin and 5-alkyl-5,10-dideazaaminopterin with the 4-substituted 1-naphthoyl group in the place of 4-substituted benzoyl. , 1996, Journal of medicinal chemistry.

[9]  I. Wilson,et al.  Towards structure-based drug design: crystal structure of a multisubstrate adduct complex of glycinamide ribonucleotide transformylase at 1.96 A resolution. , 1995, Journal of molecular biology.

[10]  D. Priest,et al.  Multifactorial resistance to 5,10-dideazatetrahydrofolic acid in cell lines derived from human lymphoblastic leukemia CCRF-CEM. , 1995, Cancer research.

[11]  E. Krug,et al.  Purine and Pyrimidine Metabolism , 1995 .

[12]  R. Christopherson,et al.  5-Aminoimidazole-4-carboxamide ribotide transformylase-IMP cyclohydrolase from human CCRF-CEM leukemia cells: purification, pH dependence, and inhibitors. , 1994, Biochemistry.

[13]  C. J. Barnett,et al.  ASYMMETRIC SYNTHESIS OF LOMETREXOL ((6R)-5,10-DIDEAZA-5,6,7,8-TETRAHYDROFOLIC ACID) , 1994 .

[14]  J. M. Hamby,et al.  Inhibitors of Glycinamide Ribonucleotide Formyltransferase as Potential Cytotoxic Agents. Synthesis of 5-Deaza-5,6,7,8-tetrahydrohomofolic Acid, 5-Deaza-5,6,7,8-tetrahydroisohomofolic Acid, and 10-Formyl-5-deaza-5,6,7,8-tetrahydroisohomofolic Acid , 1994 .

[15]  C. Yoon,et al.  Synthesis of 10-(Hydroxymethyl)-5,10-dideaza-5,6,7,8-tetrahydrofolic Acid, a Potent New Analog of DDATHF (Lometrexol) , 1994 .

[16]  S. Benkovic,et al.  Cloning and characterization of a new purine biosynthetic enzyme: a non-folate glycinamide ribonucleotide transformylase from E. coli. , 1994, Biochemistry.

[17]  R. Schultz,et al.  A novel class of monoglutamated antifolates exhibits tight-binding inhibition of human glycinamide ribonucleotide formyltransferase and potent activity against solid tumors. , 1994, Cancer research.

[18]  I. Durucasu.  The Chemistry of DDATHF (5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid) as Antitumor Agent , 1993 .

[19]  C. Shih,et al.  Synthesis and biological activity of 2-desamino and 4-deoxy analogs of 5,10-dideazatetrahydrofolic acid (DDATHF) , 1993 .

[20]  R. Ferone,et al.  Multisubstrate Analogue Inhibitors of Glycinamide Ribonucleotide Transformylase Based on 5-Deazaacyclo Tetrahudrofolate (5-DACTHF) , 1993 .

[21]  J. Barredo,et al.  A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase. , 1992, Journal of medicinal chemistry.

[22]  I. Wilson,et al.  Crystal structure of glycinamide ribonucleotide transformylase from Escherichia coli at 3.0 A resolution. A target enzyme for chemotherapy. , 1992, Journal of molecular biology.

[23]  C. Johnson,et al.  Synthesis and antifolate evaluation of 10-ethyl-5-methyl-5,10- dideazaaminopterin and an alternative synthesis of 10-ethyl-10- deazaaminopterin (edatrexate). , 1992, Journal of medicinal chemistry.

[24]  P. Gillespie,et al.  Novel 5-desmethylene analogs of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid as potential anticancer agents , 1992 .

[25]  R. Ferone,et al.  Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents. , 1992, Journal of medicinal chemistry.

[26]  S. Kerwar,et al.  Biochemical and biological studies on 2-desamino-2-methylaminopterin, an antifolate the polyglutamates of which are more potent than the monoglutamate against three key enzymes of folate metabolism. , 1992, Cancer research.

[27]  C. Shih,et al.  Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid. , 1992, Journal of medicinal chemistry.

[28]  G. Grindey,et al.  Synthesis and biological activity of nor- and homo-5,10-dideazatetrahydrofolic acid , 1992 .

[29]  Y. Shizuri,et al.  Total synthesis of (+)-isoaureothin: determination of the absolute configurations of aureothin, isoaureothin and spectinabilin , 1992 .

[30]  L. Walensky,et al.  Synthesis of 10-Substituted “Open-Chain” Analogues of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF, Lometrexol) , 1992 .

[31]  J. Peterson,et al.  Nucleotide sequence analysis of purH and purD genes from Salmonella typhimurium. , 1991, Biochimica et biophysica acta.

[32]  J. Dixon,et al.  De novo purine nucleotide biosynthesis: cloning, sequencing and expression of a chicken PurH cDNA encoding 5-aminoimidazole-4-carboxamide-ribonucleotide transformylase-IMP cyclohydrolase. , 1991, Gene.

[33]  J. Hershberger,et al.  ON THE ORIGIN OF CARBON DIOXIDE IN THE O+CH2O REACTION , 1991 .

[34]  A. Tse,et al.  Structural features of 5,10-dideaza-5,6,7,8-tetrahydrofolate that determine inhibition of mammalian glycinamide ribonucleotide formyltransferase. , 1991, Biochemistry.

[35]  E M Berman,et al.  The renewed potential for folate antagonists in contemporary cancer chemotherapy. , 1991, Journal of medicinal chemistry.

[36]  S. Benkovic,et al.  Multisubstrate adduct inhibitors of glycinamide ribonucleotide transformylase : synthetic and enzyme-assembled , 1991 .

[37]  R. Moran.  Folate antimetabolites inhibitory to de novo purine synthesis. , 1991, Cancer treatment and research.

[38]  J. Dixon,et al.  De novo purine nucleotide biosynthesis: cloning of human and avian cDNAs encoding the trifunctional glycinamide ribonucleotide synthetase-aminoimidazole ribonucleotide synthetase-glycinamide ribonucleotide transformylase by functional complementation in E. coli. , 1990, Nucleic acids research.

[39]  S. Benkovic,et al.  Active-site mapping and site-specific mutagenesis of glycinamide ribonucleotide transformylase from Escherichia coli. , 1990, Biochemistry.

[40]  E. Taylor.  New pathways from pteridines. Design and synthesis of a new class of potent and selective antitumor agents , 1990 .

[41]  P. M. Harrington,et al.  A convergent synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid and 5,10-dideaza-5,6,7,8-tetrahydrohomofolic acid. An effective principle for carbonyl group activation , 1990 .

[42]  S. Benkovic,et al.  Subcloning, characterization, and affinity labeling of Escherichia coli glycinamide ribonucleotide transformylase. , 1990, Biochemistry.

[43]  R. Ferone,et al.  Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid. , 1990, Journal of medicinal chemistry.

[44]  A. Aiba,et al.  Nucleotide sequence analysis of genes purH and purD involved in the de novo purine nucleotide biosynthesis of Escherichia coli. , 1989, The Journal of biological chemistry.

[45]  C. Shih,et al.  The 6S- and 6R-diastereomers of 5, 10-dideaza-5, 6, 7, 8-tetrahydrofolate are equiactive inhibitors of de novo purine synthesis. , 1989, The Journal of biological chemistry.

[46]  G. Wong,et al.  Convergent and efficient palladium-effected synthesis of 5, 10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF) , 1989 .

[47]  J. M. Hamby,et al.  Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogues. , 1989, Journal of medicinal chemistry.

[48]  I. Wilson,et al.  Preliminary crystallographic investigations of glycinamide ribonucleotide transformylase. , 1989, The Journal of biological chemistry.

[49]  R. Ferone,et al.  Folate analogues. 31. Synthesis of the reduced derivatives of 11-deazahomofolic acid, 10-methyl-11-deazahomofolic acid, and their evaluation as inhibitors of glycinamide ribonucleotide formyltransferase. , 1989, Journal of medicinal chemistry.

[50]  S. Benkovic,et al.  A multisubstrate adduct inhibitor of a purine biosynthetic enzyme with a picomolar dissociation constant. , 1989, Journal of medicinal chemistry.

[51]  R. Moran,et al.  A new folate antimetabolite, 5,10-dideaza-5,6,7,8-tetrahydrofolate is a potent inhibitor of de novo purine synthesis. , 1989, The Journal of biological chemistry.

[52]  J. Warner,et al.  Diels-Alder reactions of 6-azapterins. An alternative strategy for the synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF) , 1988 .

[53]  C. Caperelli.  N10-substituted 5,8-dideazafolate inhibitors of glycinamide ribonucleotide transformylase. , 1987, Journal of medicinal chemistry.

[54]  D. Ebbole,et al.  Cloning and characterization of a 12-gene cluster from Bacillus subtilis encoding nine enzymes for de novo purine nucleotide synthesis. , 1987, The Journal of biological chemistry.

[55]  S. Benkovic,et al.  Structural and mechanistic studies on the HeLa and chicken liver proteins that catalyze glycinamide ribonucleotide synthesis and formylation and aminoimidazole ribonucleotide synthesis. , 1986, Biochemistry.

[56]  S. Henikoff,et al.  A multifunctional protein possessing glycinamide ribonucleotide synthetase, glycinamide ribonucleotide transformylase, and aminoimidazole ribonucleotide synthetase activities in de novo purine biosynthesis. , 1985, Biochemistry.

[57]  R. Moran,et al.  Synthesis of the antileukemic agents 5,10-dideazaaminopterin and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin. , 1985, Journal of medicinal chemistry.

[58]  S. Benkovic,et al.  The transformylase enzymes of de novo purine biosynthesis , 1984 .

[59]  S. Benkovic,et al.  On the cofactor specificity of glycinamide ribonucleotide and 5-aminoimidazole-4-carboxamide ribonucleotide transformylase from chicken liver. , 1981, Biochemistry.

[60]  C L Krumdieck,et al.  Folylpoly-gamma-glutamates as cosubstrates of 10-formyltetrahydrofolate:5'-phosphoribosyl-5-amino-4-imidazolecarboxamide formyltransferase. , 1979, Biochemistry.

[61]  E. J. Corey,et al.  Herstellung und synthetische Verwendung von metallierten Dimethylhydrazonen Regio‐ und stereoselektive Alkylierung von Carbonylverbindungen , 1978 .

[62]  E. J. Corey,et al.  Synthesewege zu polyfunktionellen Molekülen über metallierte Dimethylhydrazone , 1978 .

[63]  J. Hynes,et al.  A new synthetic route to quinazoline analogs of folic acid , 1975 .

[64]  M. Hakala,et al.  Inhibition of the biosynthesis of 5'-phosphoribosyl-N-formylglycinamide in sarcoma 180 cells by homofolate. , 1975, Molecular pharmacology.

[65]  H. Pobiner,et al.  Solvent Effects in the Base-Catalyzed Oxidation of Ketones to Mono- and Dicarboxylic Acids , 1965 .

[66]  Y. Sprinzak,et al.  Reactions of Active Methylene Compounds in Pyridine Solution. V. α-Hydroperoxyesters , 1963 .

[67]  L. Warren,et al.  Biosynthesis of the purines. XX. Integration of enzymatic transformylation reactions. , 1957, The Journal of biological chemistry.

[68]  L. Warren,et al.  Biosynthesis of the purines. XIX. 2-Amino-N-ribosylacetamide 5'-phosphate (glycinamide ribotide) transformylase. , 1957, The Journal of biological chemistry.

[69]  J. Flaks,et al.  Biosynthesis of the purines. XVIII. 5-Amino-1-ribosyl-4-imidazolecarboxamide 5'-phosphate transformylase and inosinicase. , 1957, The Journal of biological chemistry.

[70]  L. Warren,et al.  Biosynthesis of the purines. XVII. Further studies of the inosinic acid transformylase system. , 1957, The Journal of biological chemistry.

[71]  C. Fromageot.  Chemistry and biology of pteridines: a Ciba Foundation Symposium, edited by G.E.W. Wolstenholme, J. and A. Churchill, Ltd., London. 1954. 425 pages, 42s , 1956 .