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Biomedical subjects

Henning Eickmeier

Publications and source records attributed to Henning Eickmeier.

At least 19 recordsLinked to original sources
PubMed2006

2'-Deoxy-5-propynylcytidine: a nucleoside forming two solid-state conformations.

The title compound, 4-amino-1-(2-deoxy-beta-D-erythropentofuranosyl)-5-(prop-1-ynyl)pyrimidin-2(1H)-one, C12H15N3O4, shows two conformations in the crystalline state which differ mainly in the glycosylic bond torsion angle and the sugar pucker. Both molecules exhibit an anti glycosylic bond conformation, with torsion angles chi = -135.0 (2) and -156.4 (2) degrees for molecules 1 and 2, respectively. The sugar moieties show a twisted C2'-endo sugar pucker (S-type), with P = 173.3 and 192.5 degrees for molecules 1 and 2, respectively. The crystal structure is characterized by a three-dimensional network that is stabilized by several intermolecular hydrogen bonds between the two conformers.

Crystallography, X-Ray↗
PubMed2006

9-(1,3-Anhydro-beta-D-psicofuranosyl)adenine.

In the structure of the title compound, C11H13N5O4, the glycosidic torsion angle, chi, is -107.1 (2) degrees [nucleic acid nomenclature used throughout the manuscript; IUPAC-IUB Joint Commision on Biochemical Nomenclature (1983). Eur. J. Biochem. 131, 9-15], indicating the anti conformation. The furanosyl ring adopts an N-type sugar pucker with the following pseudorotational parameters: PN = 50.5 (2) degrees and nu max = 34.9 (1) degrees. The conformation around the C5'-C6' bond is ap (gauche,trans; gt; -g), with a torsion angle gamma of 176.28 (19) degrees. The 1',2'-oxetane ring is not planar but folded along C3'...C1', with an angle of 9.6 (1) degrees.

Adenine↗
PubMed2006

2-Amino-7-chloro-2'-deoxytubercidin.

In 4-chloro-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine, C11H14ClN5O3, the conformation of the N-glycosylic bond is between anti and high-anti [chi = -102.5 (6) degrees]. The 2'-deoxyribofuranosyl unit adopts the C3'-endo-C4'-exo (3T4) sugar pucker (N-type) with P = 19.6 degrees and taum = 32.9 degrees [terminology: Saenger (1989). Landolt-Börnstein New Series, Vol. 1, Nucleic Acids, Subvol. a, edited by O. Madelung, pp. 1-21. Berlin: Springer-Verlag]. The orientation of the exocyclic C4'-C5' bond is +ap (trans) with a torsion angle gamma = 171.5 (4) degrees. The compound forms a three-dimensional network that is stabilized by four intermolecular hydrogen bonds (N-H...O and O-H...N) and one intramolecular hydrogen bond (N-H...Cl).

Crystallography, X-Ray↗
PubMed2006

7-Deaza-2,8-diazaadenosine.

In the title compound [systematic name: 4-amino-7-(beta-D-ribofuranosyl)-7H-pyrazolo[3,4-d][1,2,3]triazine], C(9)H(12)N(6)O(4), the torsion angle of the N-glycosylic bond is high anti [chi = -83.2 (3) degrees ]. The ribofuranose moiety adopts the C2'-endo-C1'-exo ((2)T(1)) sugar conformation (S-type sugar pucker), with P = 152.4 degrees and tau(m) = 35.0 degrees . The conformation at the C4'-C5' bond is +sc (gauche,gauche), with the torsion angle gamma = 52.0 (3) degrees . The compound forms a three-dimensional network that is stabilized by several hydrogen bonds (N-H...O, O-H...N and O-H...O).

Adenosine↗
PubMed2006

2'-Deoxy-7-propynyl-7-deazaadenosine: a DNA duplex-stabilizing nucleoside.

In the title compound, 2'-deoxy-7-propynyl-7-deazaadenosine, C14H16N4O3, the torsion angle of the N-glycosylic bond is anti [chi = -130.7 (2) degrees ]. The sugar pucker of the 2'-deoxyribofuranosyl moiety is C2'-endo-C3'-exo, 2T3 (S-type), with P = 185.9 (2) degrees and tau(m) = 39.1 (1) degrees , and the orientation of the exocyclic C4'-C5' bond is -ap (trans). The 7-substituted propynyl group is nearly coplanar with the heterocyclic base moiety. Molecules of the nucleoside form a layered network in which the heterocyclic bases are stacked head-to-tail with a closest distance of 3.197 (1) A. The crystal structure of the nucleoside is stabilized by three intermolecular hydrogen bonds of types N-H... O, O-H... N and O-H... O.

Crystallography, X-Ray↗
PubMed2006

N8-(2'-O-methylribofuranosyl)-8-aza-7-deazaadenine monohydrate.

In the title compound, 4-amino-2-(2-O-methyl-beta-D-ribofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine monohydrate, C11H15N5O4.H2O, the conformation of the N-glycosylic bond is syn [chi = 20.1 (2) degrees ]. The ribofuranose moiety shows a C3'-endo (3T2) sugar puckering (N-type sugar), and the conformation at the exocyclic C4'-C5' bond is -ap (trans). The nucleobases are stacked head-to-head. The three-dimensional packing of the crystal structure is stabilized by hydrogen bonds between the 2'-O-methylribonucleosides and the solvent molecules.

Adenine↗
PubMed2005

8-Aza-7-deaza-2'-deoxy-2-(methylsulfanyl)adenosine.

In the title compound, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine, C11H16N5O3S, the conformation of the glycosidic bond is between anti and high anti. The 2'-deoxyribofuranosyl moiety adopts the C3'-exo-C4'-endo conformation (3T4, S-type sugar pucker), and the conformation at the exocyclic C-C bond is +sc (+gauche). The exocyclic 6-amine group and the 2-methylsulfanyl group lie on different sides of the heterocyclic ring system. The molecules form a three-dimensional hydrogen-bonded network that is stabilized by O-H...N, N-H...O and C-H...O hydrogen bonds.

Adenosine↗
PubMed2005

2'-Deoxy-5-fluorotubercidin.

In the title compound, 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, C11H13FN4O3, the conformation of the glycosyl bond lies between anti and high anti [chi = -101.1 (3) degrees ]. The furanose moiety adopts the S-type sugar pucker (2T3), with P = 164.7 (3) degrees and tau = 40.1 (2) degrees . The extended structure is a three-dimensional hydrogen-bond network involving a C-H...F, two N-H...O and two O-H...O hydrogen bonds.

Crystallography, X-Ray↗
PubMed2005

8-Aza-7-deaza-7-propynyladenosine methanol solvate.

In the title compound, 4-amino-3-propynyl-1-(beta-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine methanol solvate, C13H15N5O4.CH3OH, the torsion angle of the N-glycosylic bond is between anti and high-anti [chi = -101.8 (5) degrees ]. The ribofuranose moiety adopts the C3'-endo (3T2) sugar conformation (N-type) and the conformation at the exocyclic C-C bond is +sc (gauche, gauche). The propynyl group is out of the plane of the nucleobase and is bent. The compound forms a three-dimensional network which is stabilized by several hydrogen bonds (O-H...O and O-H...N). The nucleobases are stacked head-to-tail. The methanol solvent molecule forms hydrogen bonds with both the nucleobase and the sugar moiety.

Adenosine↗
PubMed2005

7-Deaza-2'-deoxyguanosine.

In the title compound, 2-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, C11H14N4O4, the N-glycosylic bond torsion angle, chi, is anti [-106.5 (3) degrees ]. The 2'-deoxyribofuranosyl moiety adopts the 3T4 (N-type) conformation, with P = 39.1 degrees and tau(m) = 40.3 degrees . The conformation around the exocyclic C-C bond is ap (trans), with a torsion angle, gamma, of -173.8 (3) degrees . The nucleoside forms a hydrogen-bonded network, leading to a close-packed multiple-layer structure with a head-to-head arrangement of the bases. The nucleobase interplanar O=C-C...NH(2) distance is 3.441 (1) A.

Crystallography, X-Ray↗
PubMed2004

7-Vinyl-8-aza-7-deaza-2'-deoxyadenosine monohydrate.

In the title compound, 4-amino-1-(2-deoxy-beta-D-eythro-pentofuranosyl)-3-vinyl-1H-pyrazolo[3,4-d]pyrimidine monohydrate, C12H15N5O3.H2O, the conformation of the glycosyl bond is anti. The furanose moiety is in an S conformation with an unsymmetrical twist, and the conformation at the exocyclic C-C(OH) bond is +sc (gauche, gauche). The vinyl side chain is bent out of the heterocyclic ring plane by 147.5 (5) degrees . The three-dimensional packing is stabilized by O-H...O, O-H...N and N-H...O hydrogen bonds.

Aza Compounds↗
PubMed2004

6-Aza-2'-deoxy-2'-arabinofluorouridine, a 2'-deoxyribonucleoside with an N-sugar conformation in the solid state and in solution.

In the title compound, 2-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione, C(8)H(10)FN(3)O(5), the torsion angle of the N-glycosylic bond is anti [chi = -125.37 (13) degrees]. The furanose moiety adopts the N-type sugar pucker ((3)T(2)), with P = 359.2 degrees and tau(m) = 31.4 degrees. The conformation around the C4'-C5' bond is antiperiplanar (trans), with a torsion angle gamma of 177.00 (11) degrees. A network is formed via hydrogen bonds from the nucleobases to the sugar residues, as well as through hydrogen bonds between the sugar moieties.

Carbohydrate Conformation↗
PubMed2004

7-Deaza-2'-deoxy-7-propynylguanosine.

The title compound, C14H16N4O4, adopts the anti conformation at the glycosylic bond [chi -117.1 (5) degrees]. The sugar pucker of the 2'-deoxyribofuranosyl moiety is C2'-endo-C3'-exo, 2T3 (S-type). The orientation of the exocyclic C4'-C5' bond is +sc (gauche). The propynyl group is linear and coplanar with the nucleobase moiety. The structure of the compound is stabilized by several hydrogen bonds (N-H...O and O-H...O), leading to the formation of a multi-layered network. The nucleobases, as well as the propynyl groups, are stacked. This stacking might cause the extraordinary stability of DNA duplexes containing this compound.

Aza Compounds↗
PubMed2004

1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-4-nitro-1H-indazole.

In the title compound, C(12)H(13)N(3)O(5), the conformation of the glycosylic bond is anti [torsion angle = -105.3 (2) degrees ]. The 2'-deoxyribofuranose moiety adopts an S-type sugar pucker and the orientation of the exocyclic C-C bond is -sc (trans).

Crystallography, X-Ray↗
PubMed2003

Regioisomeric 4-nitroindazole N1- and N2-(beta-D-ribonucleosides).

The structures of the isomeric nucleosides 4-nitro-1-(beta-D-ribofuranosyl)-1H-indazole, C(12)H(13)N(3)O(6), (I), and 4-nitro-2-(beta-D-ribofuranosyl)-2H-indazole, C(12)H(13)N(3)O(6), (II), have been determined. For compound (I), the conformation of the glycosylic bond is anti [chi = -93.6 (6) degrees ] and the sugar puckering is C2'-exo-C3'-endo. Compound (II) shows two conformations in the crystalline state which differ mainly in the sugar pucker; type 1 adopts the C2'-endo-C3'-exo sugar puckering associated with a syn base orientation [chi = 43.7 (6) degrees ] and type 2 shows C2'-exo-C3'-endo sugar puckering accompanied by a somewhat different syn base orientation [chi = 13.8 (6) degrees ].

Isomerism↗