5-Bromodeoxycytidine and 5-Chlorodeoxycytidine<sup>1</sup>

Frisch, David M.; Visser, Donald W.

doi:10.1021/ja01516a058

Cited by 32 publications

(7 citation statements)

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“…1), monosubstituted in the purine ring, by nucleophilic attack of an amine nitrogen on a carbon bearing a halogen, can, in principle, be applied to the synthesis of other nucleoside or nucleotide derivatives. The synthesis of mono-bromo or monochloro derivatives ofnucleosides other than adenosine is well documented (Frisch & Visser, 1959;Michelson et al, 1962;Holmes & Robins, 1964;Wataya et al, 1973) and these could be treated in a manner analogous to that described in Scheme 1 to provide a range of mono-substituted nucleoside or nucleotide derivatives. The same general methods could also be used to convert any monophosphate into the dior tri-phosphate derivatives or to convert AMP into more complicated structures such as NAD+, FAD or CoA.…”

Section: Discussionmentioning

confidence: 99%

Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

Trayer

Small

et al. 1974

Biochemical Journal

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Methods of synthesizing a series of chemically-defined AMP, ADP, ATP, adenylyl imidodiphosphate and pyrophosphate derivatives suitable for affinity chromatography are extensively described. Each derivative has a single primary amino group at the end of a hexamethylene ;spacer' chain for attachment to CNBr-activated agarose. The synthesis of the derivative where the ;spacer' arm is attached directly to the 8 position of the adenine ring to produce 8-(6-aminohexyl)amino-AMP involves the direct bromination of AMP in the 8 position followed by displacement of the halogen by 1,6-diaminohexane. This monophosphate derivative can then be converted into the corresponding di- or triphosphate forms by direct phosphate condensation with carbonyl di-imidazole. A second series of adenosine phosphate derivatives with the phosphate moieties unsubstituted has been similarly prepared from N(6)-(6-aminohexyl)-AMP (Guilford et al., 1972). A third type of ligand has been synthesized by condensing the phosphoryl imidazolide of AMP with 6-aminohex-1-yl phosphate. This compound, P(1)-(6-aminohex-1-yl) P(2)-(5'-adenosyl) pyrophosphate, has an unsubstituted adenine ring. The synthesis of a fourth type of ligand, 6-aminohex-1-yl pyrophosphate, was done by heating 6-aminohexan-1-ol with crystalline pyrophosphoric acid under reduced pressure. The structures of the synthesized compounds were confirmed by chemical, electrophoretic and chromatographic methods and by u.v. spectrometry. The general applicability of the synthetic methods used is discussed in relation to the preparation of other affinity adsorbents. Examples are given where these derivatives have been successful in reversibly binding dehydrogenases, kinases and myosin and its proteolytic subfragments. The partial purification of rat liver glucokinase on an ADP derivative is shown.

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Section: Discussionmentioning

confidence: 99%

Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

Trayer

Small

et al. 1974

Biochemical Journal

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“…DNA, RNA, and deoxycytidine were obtained from the California Foundation for Biochemical Research. 5-Bromodeoxycytidine (Frisch and Visser, 1959) and 5-bromodeoxyuridine (Beltz and Visser, 1955) were prepared by methods previously described.…”

Section: Methodsmentioning

confidence: 99%

EFFECTS OF 5-BROMODEOXYCYTIDINE IN ESCHERICHIA COLI AND BACTERIOPHAGE

1960

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The inhibitory effects of 5-bromodeoxycytidine and 5-chlorodeoxycytidine upon growth and viability of Escherichia coli strain 15T-, a thymine requiring mutant, was described in a previous communication (Frisch and Visser, 1959). It was also reported that 5-bromodeoxycytidine produced a high frequency of plaque-type mutations in T2 bacteriophage. It has been recently demonstrated (Bessman et al., 1958) that 5bromocytosine partially replaces cytosine of deoxyribonucleic acid (DNA) formed in a cell-free

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“…Unprotected and protected nucleosides have been halogenated by direct reaction with halogens or halogenating agents. Bromination at C-5 of pyrimidine moieties was achieved by reaction of Br 2 /water [15], Br 2 /DMF [16], Br 2 /CCl 4 [17], Br 2 /CCl 4 in solvent mixture of anhydrous acetic acid and pyridine [18], N -bromosuccinimide (NBS) in DMF [19], NBS/NaN 3 in DME [20], NBS in ionic liquids [21], m -chloroperbenzoic acid (MCPBA)/HBr in DMA or DMF [22], ceric ammonium nitrate (CAN)/LiBr in AcOH or MeCN [23], KBr/potassium monoperoxysulfate under aqueous conditions [24]. Bromination of C-8 of purine moieties has been attained by reaction of Br 2 in glacial AcOH/NaOAc [25], NBS in DMF [19], Br 2 in NaOAc buffer/dioxane [10] and Br 2 in NaOAc buffer [26,27].…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Facile Methodology for Bromination of Pyrimidine and Purine Nucleosides with Sodium Monobromoisocyanurate (SMBI)

Maity

Strömberg

2013

Molecules

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5-Bromodeoxycytidine and 5-Chlorodeoxycytidine¹

Cited by 32 publications

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Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

EFFECTS OF 5-BROMODEOXYCYTIDINE IN ESCHERICHIA COLI AND BACTERIOPHAGE

An Efficient and Facile Methodology for Bromination of Pyrimidine and Purine Nucleosides with Sodium Monobromoisocyanurate (SMBI)

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5-Bromodeoxycytidine and 5-Chlorodeoxycytidine1

Cited by 32 publications

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Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

Preparation of adenosine nucleotide derivatives suitable for affinity chromatography

EFFECTS OF 5-BROMODEOXYCYTIDINE IN ESCHERICHIA COLI AND BACTERIOPHAGE

An Efficient and Facile Methodology for Bromination of Pyrimidine and Purine Nucleosides with Sodium Monobromoisocyanurate (SMBI)

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5-Bromodeoxycytidine and 5-Chlorodeoxycytidine¹