Acta Crystallographica, Section C: Crystal Structure Communications 2009-09-01

A toyocamycin analogue with the sugar moiety in a syn conformation.

Frank Seela, Sachin A Ingale, Peter Leonard, Henning Eickmeier, Hans Reuter

Index: Acta Crystallogr. C 65(Pt 9) , o431-4, (2009)

Full Text: HTML

Abstract

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.

Related Compounds

  • Toyocamycin

Related Articles:

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.

2001-03-09

[Carbohydr. Res. 331(1) , 77-82, (2001)]

Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors.

2005-02-01

[Bioorg. Med. Chem. Lett. 15(3) , 725-7, (2005)]

Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin.

2010-02-01

[J. Microbiol. Biotechnol. 20(2) , 433-7, (2010)]

Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine.

2001-01-01

[Nucleosides Nucleotides Nucleic Acids 20(10-11) , 1823-30, (2001)]

Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin.

2008-08-25

[Chem. Biol. 15(8) , 790-8, (2008)]

More Articles...