次黄嘌呤

次黄嘌呤
	首选IUPAC名; 1H-purin-6(9H)-one
识别
CAS号	68-94-0
PubChem	790
ChemSpider	768
SMILES	O=C1C2=C(NC=N2)N=CN1;
InChI	1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10);
InChIKey	FDGQSTZJBFJUBT-UHFFFAOYAJ
ChEBI	17368
KEGG	C00262
MeSH	Hypoxanthine
IUPHAR配体	4555
性质
化学式	C5H4N4O
摩尔质量	136.112 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

次黄嘌呤^[1]（hypoxanthine）又称6-羟基嘌呤（6-hydroxypurine^[2]^[3]）、6-氧嘌呤（6-oxopurine^[4]^[5]），是嘌呤碱基的代谢中间物，属于一种天然的嘌呤衍生物，广泛存在于动植物体中。它的核苷酸肌苷酸是核酸的嘌呤核苷酸的合成前体。

反应

黄嘌呤是次黄嘌呤被黄嘌呤氧化酶氧化的产物之一。在核苷酸合成中，次黄嘌呤在次黄嘌呤-鸟嘌呤磷酸核糖转移酶的作用下，转变为肌苷酸（IMP），可用于IMP的补救合成^[6]。

次黄嘌呤也是腺嘌呤发生自发脱氨的产物之一。由于它与鸟嘌呤在结构上十分相似，因此腺嘌呤的自发脱氨可导致DNA转录／复制出现错误。

制取

次黄嘌呤可由氰乙酸乙酯与乙醇钠和硫脲经成环得到2-巯基-4-氨基-6-羟基嘧啶，再经亚硝化、还原、消除、环化而得^[7]^[8]。

图片

腺嘌呤的结构。注意与次黄嘌呤的结构差别：腺嘌呤含有的是胺基，次黄嘌呤则为酮基。另注意这两幅图方向是相反的。

外部链接

醫學主題詞表（MeSH）：Hypoxanthine

^ 次黄嘌呤. 术语在线. 全国科学技术名词审定委员会. （简体中文）
^ R. L. Adams. The Biochemistry of the Nucleic Acids. Springer Science & Business Media. 2012: 6. ISBN 9789400941038.
^ Alasdair H. Neilson, Ann-Sofie Allard. Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation 2. CRC Press. 2012: 1845. ISBN 9781040187258.
^ G. W. A. Milne. Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties. John Wiley & Sons. 2005: 332. ISBN 9780471736615.
^ National Center for Biotechnology Information. PubChem Compound Summary for CID 135398638, Hypoxanthine. https://pubchem.ncbi.nlm.nih.gov/compound/Hypoxanthine. Accessed July 29, 2025.
^ Ueda S, Hirata T, Sakasegawa SI. Hypoxanthine-guanine phosphoribosyltransferase is activated via positive cooperativity between guanine and IMP. FEBS Lett. 2022;596(8):1072-1080. doi:10.1002/1873-3468.14306
^ A New Synthetic Method of 6-Hydroxypurines. Agr. Biol. Chem.
^ Sariri, R., Khalili, G. Synthesis of Purine Antiviral Agents, Hypoxanthine and 6-Mercaptopurine. Russian Journal of Organic Chemistry 38, 1053–1055 (2002). https://doi.org/10.1023/A:1020822216986

[1] 次黄嘌呤. 术语在线. 全国科学技术名词审定委员会. （简体中文）

[2] R. L. Adams. The Biochemistry of the Nucleic Acids. Springer Science & Business Media. 2012: 6. ISBN 9789400941038.

[3] Alasdair H. Neilson, Ann-Sofie Allard. Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation 2. CRC Press. 2012: 1845. ISBN 9781040187258.

[4] G. W. A. Milne. Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties. John Wiley & Sons. 2005: 332. ISBN 9780471736615.

[5] National Center for Biotechnology Information. PubChem Compound Summary for CID 135398638, Hypoxanthine. https://pubchem.ncbi.nlm.nih.gov/compound/Hypoxanthine. Accessed July 29, 2025.

[6] Ueda S, Hirata T, Sakasegawa SI. Hypoxanthine-guanine phosphoribosyltransferase is activated via positive cooperativity between guanine and IMP. FEBS Lett. 2022;596(8):1072-1080. doi:10.1002/1873-3468.14306

[7] A New Synthetic Method of 6-Hydroxypurines. Agr. Biol. Chem.

[8] Sariri, R., Khalili, G. Synthesis of Purine Antiviral Agents, Hypoxanthine and 6-Mercaptopurine. Russian Journal of Organic Chemistry 38, 1053–1055 (2002). https://doi.org/10.1023/A:1020822216986

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