二氫尿苷

二氫尿苷
	IUPAC名; 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione
別名	5,6-dihydrouridine; 1,3,5,6-tetrahydrouridine;
識別
CAS號	5627-05-4
PubChem	94312
ChemSpider	85115
SMILES	C1CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O;
InChI	1/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1;
InChIKey	ZPTBLXKRQACLCR-XVFCMESIBI
性質
化學式	C9H14N2O6
摩爾質量	246.217 g/mol g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二氫尿苷（英語：Dihydrouridine，或稱為5,6-二氫尿嘧啶核苷，縮寫D^[1]、DHU、UH₂）是一種嘧啶類核苷，由核鹼基 5,6-二氫尿嘧啶與核糖通過C-N糖苷鍵連結而成，比常見的尿苷多了兩個氫原子，使其嘧啶環上不存在碳碳雙鍵，常見於rRNA和tRNA（D環），影響其RNA結構。

由於二氫尿嘧啶沒有5(6)處的雙鍵，使得六元環不在一個平面上，D的存在擾亂了RNA螺旋與堆疊結構的穩定性。^[2]

許多在極低溫度下生活的生物（嗜冷生物）的tRNA有着較高的5,6-二氫尿嘧啶的比例（比通常的大了40-70%），增加了tRNA在低於水的冰點下的柔韌性與適應性^[3]。

參考文獻

^ IUPAC-IUB Commission on Biochemical Nomenclature. Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents. Biochemistry. 1970, 9 (20): 4022–4027. doi:10.1021/bi00822a023.
^ Dalluge JJ; Hashizume T; Sopchik AE; McCloskey JA; Davis DR. Conformational flexibility in RNA: the role of dihydrouridine. Nucleic Acids Res. Mar 15, 1996, 24 (6): 1073–1079. PMC 145759 . PMID 8604341. doi:10.1093/nar/24.6.1073.
^ Dalluge JJ; Hamamoto T; Horikoshi K; Morita RY; Stetter KO; McCloskey JA. Posttranscriptional modification of tRNA in psychrophilic bacteria. J Bacteriol. March 1, 1997, 179 (6): 1918–1923. PMC 178914 . PMID 9068636.

[1] IUPAC-IUB Commission on Biochemical Nomenclature. Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents. Biochemistry. 1970, 9 (20): 4022–4027. doi:10.1021/bi00822a023.

[2] Dalluge JJ; Hashizume T; Sopchik AE; McCloskey JA; Davis DR. Conformational flexibility in RNA: the role of dihydrouridine. Nucleic Acids Res. Mar 15, 1996, 24 (6): 1073–1079. PMC 145759 . PMID 8604341. doi:10.1093/nar/24.6.1073.

[3] Dalluge JJ; Hamamoto T; Horikoshi K; Morita RY; Stetter KO; McCloskey JA. Posttranscriptional modification of tRNA in psychrophilic bacteria. J Bacteriol. March 1, 1997, 179 (6): 1918–1923. PMC 178914 . PMID 9068636.

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