Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

Leonard, Peter; Ingale, Sachin A.; Ding, Ping; Ming, Xin; Seela, Frank

doi:10.1080/15257770903091953

Cited by 11 publications

(7 citation statements)

References 58 publications

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“…Specifically, total synthesis of toyocamycin ( 1 ) by Vorbrüggen glycosylation of ribose 5 and nucleobase 6 was firstly reported by Bobek [20], and further improved by Townsend [21], but during our many repeats of this approach [22,23,24,25], it was found that the N -9 glycosylation product 7 and N -3 glycosylation product 8 were inevitably formed simultaneously (Figure 2). This phenomenon was also reported by several other groups [26,27,28]. The selectivity and equilibrium between N -9 glycosylation product 7 and N -3 glycosylation product 8 were subsequently studied in detail [27].…”

Section: Introductionsupporting

confidence: 70%

An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

Dong

Tang

et al. 2019

Molecules

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In present paper, an expeditious total synthesis of naturally occurring 5′-deoxytoyocamycin and 5′-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.

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Section: Introductionsupporting

confidence: 70%

An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

Dong

Tang

et al. 2019

Molecules

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“…4‐Amino‐5‐cyano‐7H‐pyrrolo[2,3‐d]pyrimidine (4): 4‐Amino‐5‐cyano‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine was prepared analogous to a literature procedure 16. 4‐Amino‐6‐bromo‐5‐cyano‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine (1.60 g, 6.72 mmol) was dissolved in 300 mL ethanol and 300 mL 33% aqueous ammonium hydroxide solution.…”

Section: Methodsmentioning

confidence: 99%

Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

et al. 2012

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Abstract:The cloning, expression and characterization of a nitrile reductase (NRed) from the thermophile Geobacillus kaustophilus is reported. The enzyme shows a 12-fold increase in activity in response to a temperature change from 25 8C to 658C. The substrate scope regarding its biocatalytic applicability was investigated by testing a range of common nitriles. The narrow substrate range observed for the wild-type enzyme prompted the rational design of GkNRed active site mutants based on a previously published homology model from Bacillus subtilis. The activities of the mutants and the wild-type enzyme were investigated in their structure-function relationship regarding the natural substrate 7-cyano-7-deazaguanine (preQ 0 ) as well as a range of synthesized preQ 0 -like substrate structures. A distinct dependence of the wild-type enzyme activity on specific structural modifications of the natural substrate was observed. Two non-natural nitriles derived from preQ 0 could be reduced to their corresponding amino compounds.

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“…Compound (I) was synthesized as described by Leonard et al (2009) and crystallized from aqueous methanol. The crystals decompose above 463 K. For the diffraction experiment, a single crystal was mounted on a MiTeGen MicroMesh fiber in a thin smear of oil.…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, the crystal structure of toyocamycin was reported by Prusiner & Sundaralingam (1978). Recently, the N-3 regioisomer of toyocamycin was synthesized (Leonard et al, 2009). Generally, purine N-3 nucleosides are relatively labile molecules.…”

Section: Commentmentioning

confidence: 99%

A toyocamycin analogue with the sugar moiety in asynconformation

et al. 2009

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The title compound [systematic name: 4-amino-5-cyano-1-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine hemihydrate], C(12)H(13)N(5)O(4).0.5H(2)O, is a regioisomer of toyocamycin with the ribofuranosyl residue attached to the pyrimidine moiety of the heterocycle. This analogue exhibits a syn glycosylic bond conformation with a chi torsion angle of 57.51 (17) degrees. The ribofuranose moiety shows an envelope C2'-endo ((2)E) sugar conformation (S-type), with P = 161.6 (2) degrees and tau(m) = 41.3 (1) degrees. The conformation at the exocyclic C4'-C5' bond is +sc (gauche, gauche), with a gamma torsion angle of 54.4 (2) degrees. The crystal packing is stabilized by intermolecular O-H...O, N-H...N and O-H...N hydrogen bonds; water molecules, located on crystallographic twofold axes, participate in interactions. An intramolecular O-H...N hydrogen bond stabilizes the syn conformation of the nucleoside.

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Studies on the Glycosylation of Pyrrolo[2,3-d] Pyrimidines with 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During Toyocamycin and 7-Deazainosine Syntheses

Cited by 11 publications

References 58 publications

An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

A toyocamycin analogue with the sugar moiety in asynconformation

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