8-deaza adenines

Evidence for the formation of analogues of nicotinamide adenine dinucleotides, in which the adenine moiety is replaced by 2-aminoadenine (XLV) and 7-deaza-adenine (XLVI), from 2-aminoadenine [218] and tubercidin [202] has been presented, but the details of these biosyntheses have not been investigated. 

Fluoroadenine, 2-chloroadenine, 2-aminoadenine, 2- and 8-aza-adenines, 4-aminopyra7.olo[3, 4-d] pyrimidine and 6-methylpurine are converted to their ribonucleosidesby adenosine phosphoribosyltransferase,and their ribonucleosides are converted to the ribonucleotides by adenosine kinase most of the ribonucleotides are then converted to the di- and triphosphates. A -Aminoadenine, A -hydroxyadenine, A -methyladenine, purine, 7-deaza-adenine, and 7-amino-pyrazolo[4, 3-d] pyrimidine are either not substrates or are very poor substrates for the phosphoribosyltransferase, but their ribonucleosides are excellent substrates for the kinase. The ribonucleotides of purine, 7-deaza-adenine and... 

Selected entries from Methods in Enzymology [vol, page(s)] Determination of FMN and FAD by fluorescence titration with apoflavodoxin, 66, 217 purification of flavin-adenine dinucleotide and coenzyme A on p-acetoxymercurianiline-agarose, 66, 221 a convenient biosynthetic method for the preparation of radioactive flavin nucleotides using Clostridium kluyveri, 66, 227 isolation, chemical synthesis, and properties of roseoflavin, 66, 235 isolation, synthesis, and properties of 8-hydroxyflavins, 66, 241 structure, properties and determination of covalently bound flavins, 66, 253 a two-step chemical synthesis of lumiflavin, 66, 265 syntheses of 5-deazaflavins, 66, 267 preparation, characterization, and coenzymic properties of 5-carba-5-deaza and 1-... 

Standard methods involving glycosyl halide or ester derivatives in reaction with protected heterocycles have been applied to the synthesis of various glycosyl derivatives of 5-fluoro-uracil and -cytosine, a number of nitro-imidazoles and -pyrazoles, thiadiazines and oxadiazolo-thiadiazines, and 5-methylthio derivatives of -uracil, -4-thiouracil, and -cytosine,/3-D-ribofuranosyl derivatives of 2-thio-6-azauracil, diethyl 4-hydroxypyrazole-3,5-dicarboxylate, 5-acetyl-uraeil, 2,4- and 2,5-thiazolidinediones, 4-thiomethyl-2-azapurine, 2-hydroxypurine, 3-deaza-adenine-8- C, l-deaza-8-azaguanine, imidazo-(l,2- )l,3,5-triazenes, e.g., (5), //n-benzo-guanosine, -inosine, and -xanthosine (6), and a derivative of lV-2-(i3-D-ribopyranosyl)benzotriazoie. Likewise 2-0-... 

Unravelling the versatile metal-binding modes of adenine Looking at the molecular recognition patterns of deaza- and aza-adenines in mixed ligand metal complexes 13CCR2814. 

Tubereidin 6-amino-9-p-D-ribofuranosyl-7-deaza-purine, M, 266.25, m.p. 247-248 °C (d.), [a] j -67° (c = 1, 50% acetic acid), a purine antibiotic (see Nucleoside antibiotics) from Streptomyces tubercidicus, and one of the group of 7-deaza-adenine-nucleoside analogs. The N7 of adenine is replaced by a methylene group. T. is biosynthesized from adenosine (Fig.) the C-atoms of the pyrrole ring are derived from a ribose moiety, which is introduced from 5-phosphoribosyl 1-pyrophosphate. As an antimetabolite of adenosine, T. interferes with purine metabolism. T. can also be eonverted into nicotinamide-dea-za-adenine dinucleotide, which inhibits glycolysis. T. is particularly active against Mycobacterium tuberculosis and Candida albicans. 

I. Antonini, G. Cristalli, P. Franchetti, M. Grifantini, S. Martelli, G. Lupidi, and F. Riva, Adenosine deaminase inhibitors. Synthesis of deaza analogues of erythro-9-(2-hydioxy-3-nonyl)adenine, J. Med. Chem. 27 274 (1984). 

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