NEIDLE, S; KAYE, A; REESE, C; (1990) X-RAY STRUCTURAL STUDIES ON 3 ANALOGS OF THE ALPHA-ANOMER OF THE ANTITUMOR ANTIBIOTIC SHOWDOMYCIN - DIFFERENTIAL RING-PUCKERING EFFECTS OF HYDROXYL SUGAR SUBSTITUENTS IN LYXO AND ARABINO CONFIGURATIONS. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE , 46 (Part 3) 426 - 431. 10.1107/S0108768190000866.

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Abstract

The crystal structures of three a-analogues of the anititumour antibiotic showdomycin (1) have been determined at room temperature. They are 2-(a-D-2'- deoxyribofuranosyl)maleimide (2), 2-(a-D-arabinofuranosyl) maleimide (3) and 2-(a-D-lyxofuranosyl)- maleimide (4). The structures were refined to R factors of 0-039, 0-042 and 0-029 for 971, 1025 and 716 observed reflections. The conformational properties of the sugar rings are discussed in detail, in relation to the differing hydroxyl group substitutions. Compounds (2) and (3) have CY-endo, C4"-exo and CY-endo ring puckers, whereas (3) has C2"-endo, C l'-exo puckers. Compound (3) has an intramolecular hydrogen bond between the 05' and 02' hydroxyl groups. This and the sugar pucker difference are in accord with NMR chemical shift data for the O5' and O2' protons. Crystal data: compound (2), C9H11NOs, orthorhombic, P212~21, a = 5-916 (1), b = 8-191 (1), c = 19.691 (3) A, Z = 4; compound (3), C9HIINO6, orthorhombic, P212121, a = 6.785 (1), b = 8.006 (1), c = 17.564 (2) A, Z= 4; compound (4), C9HI1NO6, monoclinic, P2~, a = 8.681 (1), b = 5.135 (1), c= 11-364 (1) A, Z= 2.

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