The N-7 regioisomer of 2-chloro-2′-deoxyadenosine: synthesis, crystal structure, conformation, and stability

Worthington, V. L.; Fraser, W. Hamish; Schwalbe, Carl H.

doi:10.1016/0008-6215(95)00168-s

Cited by 8 publications

(9 citation statements)

References 24 publications

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“…The residue was dissolved in ethanol, absorbed on silica gel (2 mL), and put on the top of the silica gel column (2 × 19 cm), which was then eluted with 5 → 20% MeOH/CHCl 3 (v/v) to afford cladribine (10 mg, 59%) that was identical with a standard sample. The 1 H and 13 C NMR spectra in DMSO- d 6 of this product were consistent with literature data [ 81 ].…”

Section: Methodssupporting

confidence: 89%

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

Artsemyeva¹,

Remeeva²,

Buravskaya³

et al. 2020

Beilstein J. Org. Chem.

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In the present work, we suggested anion exchange resins in the phosphate form as a source of phosphate, one of the substrates of the phosphorolysis of uridine, thymidine, and 1-(β-ᴅ-arabinofuranosyl)uracil (Ara-U) catalyzed by recombinant E. coli uridine (UP) and thymidine (TP) phosphorylases. α-ᴅ-Pentofuranose-1-phosphates (PF-1Pis) obtained by phosphorolysis were used in the enzymatic synthesis of nucleosides. It was found that phosphorolysis of uridine, thymidine, and Ara-U in the presence of Dowex® 1X8 (phosphate; Dowex-nPi) proceeded smoothly in the presence of magnesium cations in water at 20–50 °C for 54–96 h giving rise to quantitative formation of the corresponding pyrimidine bases and PF-1Pis. The resulting PF-1Pis can be used in three routes: (1) preparation of barium salts of PF-1Pis, (2) synthesis of nucleosides by reacting the crude PF-1Pi with an heterocyclic base, and (3) synthesis of nucleosides by reacting the ionically bound PF-1Pi to the resin with an heterocyclic base. These three approaches were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52–93%).

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Section: Methodssupporting

confidence: 89%

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

Artsemyeva¹,

Remeeva²,

Buravskaya³

et al. 2020

Beilstein J. Org. Chem.

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“…This conformation was also observed for the hydroxy group of (IV) ( = 57.8 ; Worthington et al, 1995). This conformation was also observed for the hydroxy group of (IV) ( = 57.8 ; Worthington et al, 1995).…”

Section: Commentsupporting

confidence: 72%

“…According to Steiner (2002), for bifurcated hydrogen bonds with distinctly different hydrogen-acceptor separations, the shorter interaction is defined as the major component and the longer one as the minor. A similar intramolecular bifurcated hydrogenbonding pattern was also observed in the crystal structures of 2-chloro-2 0 -deoxyadenosine, (IV) (Worthington et al, 1995), and 2 0 -deoxy-5-methylisocytidine, (V) (Seela et al, 2000). The minor component utilizes atom O4 0 as acceptor, with N6Á Á ÁO4 0 = 3.1676 (15) Å and N6-H6BÁ Á Á O4 0 = 143 .…”

Section: Commentsupporting

confidence: 69%

“…We report here the conformation and hydrogen bonding of (I) in the crystalline state and compare the structure with those of the related molecules of 8-azaadenosine, (IIb) (Singh & Hodgson, 1974, 1977, 8-aza-7-deaza-2 0 -deoxyadenosine, (III) (Seela et al, 1999), and the N-7 regioisomer of 2-chloro-2 0 -deoxyadenosine, (IV) (Worthington et al, 1995). The threedimensional structure of (I) is shown in Fig.…”

Section: Commentmentioning

confidence: 97%

“…The corresponding torsion angle in (I), (O4 0 -C1 0 -N7-C5) = 64.17 (16) , reflects a syn conformation. In this case, the syn conformation ( = 67.0 ) is also stabilized by a bifurcated intramolecular hydrogen bond, with atom H6 of the amino group as donor and atoms O5 0 and O4 0 of the glycon as acceptors (Worthington et al, 1995). However, inspection of the hydrogen-bonding pattern of (I) reveals a bifurcated intramolecular hydrogen bond between the amino group of the nucleobase and atoms O5 0 and O4 0 of the sugar moiety, imposing the syn conformation of nucleoside (I).…”

Section: Commentmentioning

confidence: 99%

See 2 more Smart Citations

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

Jiang

Budow

et al. 2010

Acta Crystallogr C

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The title compound, C(9)H(12)N(6)O(3), shows a syn-glycosylic bond orientation [χ = 64.17 (16)°]. The 2'-deoxyfuranosyl moiety exhibits an unusual C1'-exo-O4'-endo ((1)T(0); S-type) sugar pucker, with P = 111.5 (1)° and τ(m) = 40.3 (1)°. The conformation at the exocyclic C4'-C5' bond is +sc (gauche), with γ = 64.4 (1)°. The two-dimensional hydrogen-bonded network is built from intermolecular N-H...O and O-H...N hydrogen bonds. An intramolecular bifurcated hydrogen bond, with an amino N-H group as hydrogen-bond donor and the ring and hydroxymethyl O atoms of the sugar moiety as acceptors, constrains the overall conformation of the nucleoside.

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ChemInform Abstract: The N‐7 Regioisomer of 2‐Chloro‐2′‐deoxyadenosine: Synthesis, Crystal Structure, Conformation, and Stability.

1996

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The N-7 regioisomer of 2-chloro-2′-deoxyadenosine: synthesis, crystal structure, conformation, and stability

Cited by 8 publications

References 24 publications

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

ChemInform Abstract: The N‐7 Regioisomer of 2‐Chloro‐2′‐deoxyadenosine: Synthesis, Crystal Structure, Conformation, and Stability.

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