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G V Gurskaia

Publications and source records attributed to G V Gurskaia.

11 recordsLinked to original sources
PubMed1995

[3'-(Tetrazol-2''-yl-3'-deoxythymidine and its 5''-substituted form: synthesis and conformation in the crystalline state. Substrate properties of 3'-(tetrazol-2''-yl)-3'-deoxythymidine-5'-triphosphate in relation to DNA polymerases].

5''-Derivatives of 3'-(tetrazole-2''-yl)-3'-deoxythymidines were synthesized by interaction of 5'-benzoyl-2',3'-anhydrothymidine with tetrazole or its 5-derivatives followed by debenzoylation. Structures of two of them, 3'-(tetrazole-2''-yl)-3'-deoxythymidine and 3'-(5''-methyltetrazole-2''-yl)-3'-deoxythymidine, elucidated by X-ray analysis, revealed anti conformation of thymine about the glycosidic bond and 2'-endo-3'-exo-conformation of the sugar residue with gauche+ orientation with respect to C4'-C5'-bond. 3'-(Tetrazole-2''-yl)-3'-deoxythymidine 5'-triphosphate demonstrated poor substrate properties for the avian myeloblastosis virus reverse transcriptase and none for several other DNA polymerases.

Base Sequence↗
PubMed1995

[X-ray structural study of 3'-O-methylthiomethylthymidine and 3'-O-methylsulfinylmethylthymidine--potential inhibitors of HIV].

The molecular and crystalline structures of deoxiribonucleoside analogs: 3'-O-methylthiomethylthymidine monohydrate dT(CH2SMe).H2O and 3'-O-methylsulphinylmethylthymidine dT(CH2SOMe) were determined. The space group of dT(CH2SMe).H2O crystals is P2(1), the parameters of the elementary cell are a = 10.417(1), b = 4.912(2), c = 15.969(2) A, beta = 107.23(1) degrees, V = 780.5 A3, Z = 2, R = 3.8%. The crystals of dT(CH2SOMe have a space group P2(1)2(1)2(1), the elementary cell parameters are a = 8.858(2), b = 9.303(1), c = 17.698(2) A, V = 1458.3 A3, Z = 4, R = 2.8%. The dT(CH2SMe) and dT(CH2SOMe) molecules are characterized by an anti-conformation relative to the glycoside bond (angles chi (O4'-C1'-N1-C2) are equal to -116.2 degrees and -148.8 degrees), a gauche(+)-conformation relative to the exocyclic bond C4'-C5' (angles phi CO (C3'-C4'-C5'-O5') are equal to 52.1 degrees and 41.1 degrees). The conformation of the furanose cycle in the dT(CH2SMe) molecule is described by C2'-endo-C3'-exo (P = 167.8 degrees, psi m = 34.8 degrees) and in the dT(CH2SOMe) molecule by C2'-endo-C1'-exo (P = 148.4 degrees, psi m = 35.4 degrees). The structures studied were compared with 3'-azido-3'-deoxythymidine (AZT) and thymidine.

Antiviral Agents↗
PubMed1992

[Molecular and crystalline structure of 3'-methylamino-2',3'-dideoxyribosylthymine--a potential inhibitor of HIV].

The structure of 3'-methylamino-2',3'-dideoxyribosylthymine [ddT(3'NHMe)] was determined by X-ray analysis. The space group is P2(1)2(1)2(1). Cell dimensions are: a 5.132(1), b 13.718(1), c 16.947(2) A, V 1193.2 A3, Z 4. The structure was solved by directed methods and refined by the full-matrix least square method to R 4.8%. The molecule of ddT(3'NHMe) has anti-conformation with respect to the glycosidic bond (chi (O4'-C1'-N1-C2) = -106.7 degrees), C3'-endo-C4'-exo puckering of the sugar moiety (P -28.8 degrees, psi m -31.5 degrees) and gauche-gauche conformation about exocyclic C4'-C5' bond (psi(C3'-C4'-C5'-O5') 45.8 degrees). The structure of ddT(3'NHMe) was compared with those of 3'-amino-3'-deoxythymidine, 3'-azido-3'-deoxythymidine and natural thymidine.

Antiviral Agents↗
PubMed1988

[The structure and antiviral activity of ribavirin analogs. II. Molecular and crystal structure of 1-(1,5-dihydroxy-3-oxapent-2-yl)-1,2,4-triazole-5-carboxamide].

X-ray structure of the title compound, an antiviral agent moderately active towards Herpes simplex virus type 1, has been determined. The space group is P2i/n, unit cell parameters: a = 10,119, b = 7,529, c = 13,585 A, beta = 107,82 degrees, Z = 4. The structure was solved by the direct method and refined by least-squares procedure to R = 2.9%. The gauche-conformation about C4'-C5' bond and trans-conformation about O4'-C4' bond are realized in the molecule. The carboxyamide group at the C5 atom of triazol cycle provides a steric opportunity for the intramolecular hydrogen bond C1'-H1'...O6 formation.

Antiviral Agents↗
PubMed1988

[The structure and antiviral activity of ribavirin analogs. I. Molecular and crystal structure of 1-(2-hydroxyethoxymethyl)-1,2,4-triazole-5-carboxamide].

The crystal and molecular structures of the antiviral compound 1-(2-hydroxyethoxymethyl)-1,2,4-triazole-5-carboxamide has been determined by the X-ray diffraction method. The space group is P2i/c, unit cell parameters a = 4,381, b = 18,679, c = 10,776 A, beta = 107,40 degrees, Z = 4. The structure was solved by the direct method and refined by a full-matrix least-squares procedure to R = 4.9%. Two planar groups of atoms can be distinguished in the molecule. The first group involves the atoms of triazole ring, C6, and C1', the second one contains C5, C6, O6 and N6 atoms. The angle between these planes is 5.6 degrees. The carboxyamide group is rotated by 180 degrees in comparison with this group in ribavirin. That is why the intramolecular hydrogen bond C1'-H1'. 1...O6 can form. Torsion angle O5'-C5'-C4'-O4' is 73.9 degrees and it corresponds to gauche-rotamer. The conformation about O4'-C4' bond is trans. The C1'-C4' bond is approximately perpendicular to the aglycone.

Acyclovir↗
PubMed1988

[The structure and antiviral activity of ribavirin analogs. III. Molecular and crystal structure of 1-(2-hydroxyethoxymethyl)-1,2,4-triazole-carboxamide].

The crystal and molecular structure of a ribavirin acyclic analogue, 1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide, has been determined by X-ray diffraction method. The space group is P1, unit cell parameters: a = 5,237, b = 6,960, c = 11,483 A, alpha = 93,89, beta = 97,43, gamma = 94,26 degrees; Z = 2. The structure was solved by the direct method and refined by least-squares procedure to R = 3.7%. Two molecular conformers statistically coexist in the unit cell, differing in the hydroxyethoxymethyl group conformation. Trans-conformation about O4'-C4' bond and gauche about C4'-C5' bond are observed in both molecules. C1'-O4' bond is approximately perpendicular to the aglicon.

Antiviral Agents↗
PubMed1984

[X-ray study of an antiviral agent (S)-9-(2,3-dihydroxypropyl)adenine].

The molecular and crystal structures of the antiviral compound, (S)-9-(2,3-dihydroxypropyl)adenine, was established. The space group is P21, unit-cell parameters a 5,546(1), b 8,381(1), c 10,119(1), beta 91,979(9) degrees, Z2. The structure was solved by the direct method and refined by a full-matrix least-squares procedure to R 4,2%. All non-hydrogen atoms of this compound are concentrated in two planes. The first one involves the atoms of the purine moiety and N(6) and C(1'), while the second one accommodates C(2'), C(3'), O(2') and O(3'). The angle between these planes is 54,3 degrees. The conformation of the compound in crystal was compared with that deduced from theoretical analysis.

Adenine↗
PubMedDate not supplied

[Interdomain interactions in aspartic proteases of higher organisms and their analogs in retroviral enzymes].

A continuous chain of hydrogen bonded groups, which forms cross-hands interaction between domains in molecules of pepsin-like enzymes, has been revealed. The chain contains a pair of 6 symmetrically related hydrogen bonds between main chain atoms and the two conserved water molecules. The peptide groups forming hydrogen bond with the inner oxygens of the active carboxyls are important elements of the chain. The so-called "fireman grip" hydrogen bonding, consisting of a pair of the two symmetrically related bonds, is an integral part of this system of interactions. One of the water molecules in this system has a zero accessibility and forms a very short hydrogen bond with the active site interacting peptide group. This chain connects tightly the two regions of domains which have a high correlation in conformational mobility. The retroviral enzymes have an abortive chain of the interdomain interaction in this region which is reduced to the "fireman grip" net.

Animals↗
PubMedDate not supplied

[Conformation of crystalline 3'-nitro-2',3'-dideoxythymidine and properties of its 5'-triphosphate as a terminator substrate of retroviral reverse transcriptase].

The structure of new nucleoside--3'-nitro-2',3'-dideoxythymidine (NIT) possessing moderate anti HIV activity in MT-4 cell culture was investigated by X-ray analysis. These data showed that conformation of NIT in crystal is similar to that of one of crystallographically independent forms of 3'-azido-2',3'-dideoxythymidine. 3'-Nitro-2',3'-dideoxythymidine 5'-triphosphate (NITTP) was synthesized and its ability to inhibit human and viral DNA polymerases was studied. NITTP proved to be effective and highly selective terminating substrate of DNA synthesis catalyzed by HIV and AMV reverse transcriptases. Human DNA polymerase alpha as well as DNA polymerase beta (rat liver), terminal deoxynucleotidyltransferase (calf thymus) or HSV-1 and CMV DNA polymerases did not incorporate NITTP into a growing DNA chain.

Animals↗