Synchrotron Powder Diffraction, X-ray Absorption and 1H Nuclear Magnetic Resonance Data for Hypoxanthine, C5H4N4O


  1. Reid, J.
  2. Wang, S.
  3. Bond, T.
  4. Zhou, J.
  5. Hu, A.
Corporate Authors
Defence Research and Development Canada, Suffield Research Centre, Ralston AB (CAN)
Hypoxanthine is a natural purine derivative and deamination product of adenine [C5H5N5, one of the two purine bases found in deoxyribonucleic acid (DNA), and ribonucleic acid (RNA)], forming as an intermediate product prior to uric acid (C5H4N4O3) during metabolic breakdown (Sarkar and Nahar, 2007). Defects in purine metabolism can result in significant uptake of hypoxanthine in DNA and RNA, which may impede RNA function and gene expression (Pang et al., 2012), and hypoxanthine has been observed as a constituent in riboswitches, which acts as control mechanisms for cellular metabolism (Batey et al., 2004). The levels of purine metabolites are highly regulated in the body and hypoxanthine imbalances may be linked with numerous issues from the formation of crystalline hypoxanthine in muscle tissue (Parker et al., 1969) to the occurrence of gout (Puig et al., 1988). The structure of hypoxanthine was originally determined by Schmalle et al. (1988) using single-crystal X-ray diffraction (XRD). Figure 1 shows the structure, corresponding to the keto N9H tautomer, illustrating two crystallographically independent molecules (molecules A and B) in the triclinic unit cell. Currently, a single low-precision, unindexed, experimental powder diffraction pattern appears for hypoxanthine in the Powder Diffraction File (ICDD, 2013) (PDF 00-007-0712), although an additional pattern (PDF 02-064-3532) calculated from the crystal structure of Schmalle et al. (1988) is included in the PDF-4 Organi
NMR;XRD;chemical and biological;detection and identification
Report Number
DRDC-RDDC-2015-P112 — External Literature
Date of publication
01 Sep 2015
Number of Pages
Electronic Document(PDF)

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