Ślepokura Katarzyna, Mitaszewska Irmina
Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Street, 50-383 Wrocław, Poland.
Acta Crystallogr C. 2011 May;67(Pt 5):o161-5. doi: 10.1107/S0108270111011723. Epub 2011 Apr 13.
The six-membered cyclic phosphate diester, 5,5-dimethoxy-2-hydroxy-1,3,2-dioxaphosphorinan-2-one, C(5)H(11)O(6)P or (MeO)(2)cDHAP, which is the dimethyl acetal of cyclic dihydroxyacetone phosphate (cDHAP), has been obtained in the form of two new cyclohexylammonium (cha) salts, cyclohexylammonium 5,5-dimethoxy-2-oxo-1,3,2-dioxaphosphorinan-2-olate monohydrate, (cha)[(MeO)(2)cDHAP]·H(2)O or C(6)H(14)N(+)·C(5)H(10)O(6)P(-)·H(2)O, and cyclohexylammonium 5,5-dimethoxy-2-oxo-1,3,2-dioxaphosphorinan-2-olate, (cha)[(MeO)(2)cDHAP] or C(6)H(14)N(+)·C(5)H(10)O(6)P(-), as well as in the form of the anhydrous free acid, (MeO)(2)cDHAP. It is shown that protonation of the cyclic phosphate group influences the chair conformation of the P/O/C/C/C/O 1,3,2-dioxaphosphorinane ring, and that differences in the ring conformation correlate with different deformations observed in the ionized and protonated phosphate groups. The ring is more evenly puckered in the anions, in contrast with the flattening observed in the structure of the free acid.
六元环状磷酸二酯，5,5 - 二甲氧基 - 2 - 羟基 - 1,3,2 - 二氧磷杂环己烷 - 2 - 酮，C(5)H(11)O(6)P或(MeO)(2)cDHAP，它是环状二羟基丙酮磷酸酯（cDHAP）的二甲基缩醛，已以两种新的环己基铵（cha）盐的形式获得，即环己基铵5,5 - 二甲氧基 - 2 - 氧代 - 1,3,2 - 二氧磷杂环己烷 - 2 - 醇一水合物，(cha)[(MeO)(2)cDHAP]·H(2)O或C(6)H(14)N(+)·C(5)H(10)O(6)P(-)·H(2)O，以及环己基铵5,5 - 二甲氧基 - 2 - 氧代 - 1,3,2 - 二氧磷杂环己烷 - 2 - 醇，(cha)[(MeO)(2)cDHAP]或C(6)H(14)N(+)·C(5)H(10)O(6)P(-)，还以无水游离酸(MeO)(2)cDHAP的形式获得。结果表明，环状磷酸基团的质子化影响P/O/C/C/C/O 1,3,2 - 二氧磷杂环己烷环的椅式构象，并且环构象的差异与在离子化和质子化的磷酸基团中观察到的不同变形相关。与游离酸结构中观察到的扁平状相比，阴离子中环的褶皱更均匀。
