Synthesis of adenine 5'-O-sulfamoyl nucleosides related to nucleocidin

Shuman, Dennis A.; Rk, Robbins; Mj, Robins

doi:10.1021/ja01040a062

Cited by 43 publications

(22 citation statements)

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“…Initial geometries were obtained by AM1 13 quantum-mechanical semiempirical calculations by using the original parameters of this program, based on the restricted Hartree-Fock (RHF) method, included in MOPAC version 6.0.…”

Section: Methodsmentioning

confidence: 99%

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?-Caprolactone/ZnCl2 complex formation: Characterization and ring-opening polymerization mechanism

Abraham

Gallardo

Lozano

et al. 2000

J. Polym. Sci. A Polym. Chem.

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Section: Methodsmentioning

confidence: 99%

“…1 H and 13 C nuclear magnetic resonance spectra of the monomer/initiator mixtures were performed in a Varian XLR-300 NMR spectrometer operating at 75.5 MHz for 13 C and 300 MHz for 1 H measurements. NMR measurements of bulk samples were performed at 80°C (melting point 60 -65°C).…”

Section: Characterizationmentioning

confidence: 99%

?-Caprolactone/ZnCl2 complex formation: Characterization and ring-opening polymerization mechanism

Abraham

Gallardo

Lozano

et al. 2000

J. Polym. Sci. A Polym. Chem.

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“…by modification of the methods of Shuman et al (14). 2Ј,3Ј-O-Isopropylidene-5Ј-O-sulfamoyladenosine was first purified as follows.…”

Section: Synthesis Of Inhibitors-5ј-o-sulfamoyladenosine Was Synthesizedmentioning

confidence: 99%

Biochemical, Crystallographic, and Mutagenic Characterization of Hint, the AMP-Lysine Hydrolase, with Novel Substrates and Inhibitors

Krakowiak

Pace

Blackburn

et al. 2004

Journal of Biological Chemistry

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Hint, histidine triad nucleotide-binding protein, is a universally conserved enzyme that hydrolyzes AMP linked to lysine and, in yeast, functions as a positive regulator of the RNA polymerase II C-terminal domain kinase, Kin28. To explore the biochemical and structural bases for the adenosine phosphoramidate hydrolase activity of rabbit Hint, we synthesized novel substrates linking a p-nitroaniline group to adenylate (AMP-pNA) and inhibitors that consist of an adenosine group and 5-sulfamoyl (AdoOSO 2 NH 2 ) or N-ethylsulfamoyl (AdoOSO 2 NHCH 2 CH 3 ) group. AMP-pNA is a suitable substrate for Hint that allowed characterization of the inhibitors; titration of each inhibitor into AMP-pNA assays revealed their K i values. The N-ethylsulfamoyl derivative has a 13-fold binding advantage over the sulfamoyl adenosine. The 1.8-Å cocrystal structure of rabbit Hint with N-ethylsulfamoyl adenosine revealed a binding site for the ethyl group against Trp-123, a residue that reaches across the Hint dimer interface to interact with the alkyl portion of the inhibitor and, presumably, the alkyl portion of a lysyl substrate. Ser-107 is positioned to donate a hydrogen bond to the leaving group nitrogen. Consistent with a role in acid-base catalysis, the Hint S107A mutant protein displayed depressed catalytic activity.

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“…The first fluorinated microbial metabolite to be reported was nucleocidin, an antibiotic nucleoside isolated from Streptomyces calvus. While the metabolite was first isolated in 1957 (Thomas et al 1957), the correct structure was not proposed until 12 years later (Shuman et al 1969), before being confirmed by total synthesis (Jenkins et al 1976). While the intriguing structure has attracted attention, numerous attempts to re-isolate nucleocidin from S. calvus strains have proved unsuccessful (Maguire et al 1993).…”

Section: Importance Of Fluorine In Pharmaceutical Compoundsmentioning

confidence: 99%

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Murphy

Clark

Amadio

2009

Appl Microbiol Biotechnol

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Publication information Applied Microbiology and Biotechnology, 84 (4): 617-629Publisher Springer Item record/more information http://hdl.handle.net/10197/5314 Publisher's statementThe final publication is available at www.springerlink.com can lead to the generation of toxic compounds that are of environmental concern, yet similar biotransformations can yield difficult-to-synthesise products and intermediates, in particular derivatives of biologically active secondary metabolites. In this paper we review the historical and recent developments of organofluorine biotransformation in microorganisms, and highlight the possibility of using microbes as models of fluorinated drug metabolism in mammals.3

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Synthesis of adenine 5'-O-sulfamoyl nucleosides related to nucleocidin

Cited by 43 publications

References 0 publications

?-Caprolactone/ZnCl2 complex formation: Characterization and ring-opening polymerization mechanism

?-Caprolactone/ZnCl2 complex formation: Characterization and ring-opening polymerization mechanism

Biochemical, Crystallographic, and Mutagenic Characterization of Hint, the AMP-Lysine Hydrolase, with Novel Substrates and Inhibitors

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

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