Chemical Properties
Crystalline
Uses
2′-Deoxyinosine has been used in the quantification of nucleoside forms of DNA lesion in a single DNA sample by liquid chromatography tandem mass spectrometry (LC-MS/MS). It has also been used as a standard for high performance liquid chromatography analysis.
Uses
An Inosine (I661000) analog with hypotensive activity. An impurity of the antiviral drug 2’,3’-Dideoxyinosine (D440950).
Definition
ChEBI: 2'-deoxyinosine is a purine 2'-deoxyribonucleoside that is inosine in which the hydroxy group at position 2' is replaced by a hydrogen. It has a role as a Saccharomyces cerevisiae metabolite, a human metabolite, a plant metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside. It is functionally related to an inosine.
Biochem/physiol Actions
2′-Deoxyinosine is a nucleoside form of hypoxanthine. It is a DNA damage product resulting from the impairment of DNA by reactive nitrogen species. 2′-deoxyinosine is formed from nitrosative deamination by N2O3.
Synthesis
2'-Deoxyinosine is produced via a microbial one-pot process using glucose, acetaldehyde, and adenine as substrates. In an E. coli BL21/pTS17 system utilizing enzymatically prepared 2-deoxyribose 5-phosphate, adenine serves as the nucleobase precursor to yield 2'-deoxyinosine as the sole deoxyribonucleoside product. This biochemical retrosynthesis route achieves a molar yield of 17.7% relative to glucose[1][2].
Purification Methods
2'-Deoxyinosine [890-38-0] M 252.2, m 206o(dec), 218-220o(dec), [ ] D25 -21o (c 2, N ] D -21o (c 1, H 2O), pKEst(1) ~ 8.9, pKEst(2) ~ 12.4. Purify 2'-deoxyinosine by recrystallisation from H2O. [Brown & Lythgoe J Chem Soc 1990 1950, UV: MacNutt Biochem J 50 384 1952, Beilstein 26 III/IV 2086.]
References
[1] Horinouchi, N., Ogawa, J., Kawano, T., Sakai, T., Saito, K., Matsumoto, S., Sasaki, M., Mikami, Y., & Shimizu, S. (2005). Biochemical retrosynthesis of 2′-deoxyribonucleosides from glucose, acetaldehyde, and a nucleobase. Applied Microbiology and Biotechnology, 71(5), 615–621.
https://doi.org/10.1007/s00253-005-0205-5 [2] Horinouchi, N., Ogawa, J., Kawano, T., Sakai, T., Saito, K., Matsumoto, S., Sasaki, M., Mikami, Y., & Shimizu, S. (2006). One-pot Microbial Synthesis of 2′-deoxyribonucleoside from Glucose, Acetaldehyde, and a Nucleobase. Biotechnology Letters, 28(12), 877–881.
https://doi.org/10.1007/s10529-006-9019-5
