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嘌呤

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嘌呤
IUPAC名
9H-purine
识别
CAS号 120-73-0  ✓
PubChem 1044
ChemSpider 1015
SMILES
InChI
InChIKey KDCGOANMDULRCW-UHFFFAOYAO
ChEBI 17258
KEGG C15587
MeSH Purine
性质
化学式 C5H4N4
摩尔质量 120.112 g·mol⁻¹
熔点 214 °C
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

piào[註 1]lìngC5H4N4,英语:Purine),又译普林,是新陈代谢过程中的一种代谢物。它是一种带有四个原子的杂环芳香有机化合物,嘌呤和嘧啶核酸中最重要的组成部分。

如果身体未能将嘌呤进一步代谢并从肾脏中经尿液排出的话,而这些物质最终形成尿酸,再经血液流向软组织,以结晶体积存于其中,假若有诱因[需要解释]引起沉积在软组织如关节膜或肌腱里的尿酸结晶释出,那便导致身体免疫系统过度反应(敏感)而造成炎症(痛风症)。

衍生物

许多嘌呤衍生物存在于自然界,核苷酸五种碱基中的两种为嘌呤衍生物:腺嘌呤鸟嘌呤。在DNA中,两条链上的碱基根据碱基互补配对原则以氢键结合,腺嘌呤与胸腺嘧啶,鸟嘌呤与胞嘧啶。在RNA,尿嘧啶取代胸腺嘧啶。

其他重要嘌呤衍生物有次黄嘌呤黄嘌呤茶碱可可碱咖啡因尿酸异鸟嘌呤

Purines.svg

生物功能

除了腺嘌呤和鸟嘌呤在DNA和RNA中的重要作用,嘌呤衍生物还存在于许多其它重要的生物分子,如ATPGTP,环状AMP,NADH辅酶A。嘌呤本身未在自然界中发现,需通过有机合成制备。

嘌呤衍生物还可作为神经递质,与嘌呤受体作用,例如腺苷激活腺苷受体

历史

“嘌呤”(purine)一词意为纯尿(pure urine[1],最早由德国化学家埃米尔·费歇尔于1884年提出。他于1899年首次合成了此化合物。[2]合成路线的起始物质是尿酸 (8),此物质最早由舍勒于1776年从肾结石中提取。[3]尿酸(8)与PCl5反应得2,6,8-三氯嘌呤(10),后者与HIPH4I反应得2,6-二碘嘌呤(11)。用锌粉还原得嘌呤(1)。天然嘌呤衍生物分子量比吡啶衍生物大很多。

FischerPurineSynthesis.gif

实验室合成

嘌呤在生物体内的合成可以人工实现。甲酰胺在开口容器中以170 °C加热28小时,可得到可观产率的嘌呤:[4]

Purinesynthesis-en.svg

这个重要的反应是生命起源的讨论内容,因其由小分子有机物生成,而嘌呤的衍生物构成遗传物质DNA和RNA的碱基。[5]

Oro, Orgel等人发现四分子HCN缩合生成二氨基丁烯二腈(diaminomaleodinitrile,12),后者与其它小分子反应能得到自然界存在的大多数嘌呤衍生物。[6][7][8][9][10]

Basicpurines.png

陶贝合成法 (1900)是一种经典的合成嘌呤的方法。其中成嘌呤环的一步是胺取代吡啶与甲酸的反应:[11]

Traube purine synthesis

参考资料

  1. ^ McGuigan, Hugh. An Introduction To Chemical Pharmacology. P. Blakiston's Sons & Co. 1921: 283 [July 18, 2012]. (原始内容存档于2020-04-16). 
  2. ^ Fischer, E. Berichte der Deutschen Chemischen Gesellschaft 1899, 32, 2550.
  3. ^ Scheele, V. Q. Examen Chemicum Calculi Urinari, Opuscula, 1776, 2, 73.
  4. ^ Yamada, H.; Okamoto, T. A One-step Synthesis of Purine Ring from Formamide. Chemical & Pharmaceutical Bulletin. 1972, 20 (3): 623 [2014-02-25]. doi:10.1248/cpb.20.623. (原始内容存档于2016-05-16). 
  5. ^ Saladino; Crestini, Claudia; Ciciriello, Fabiana; Costanzo, Giovanna; Mauro, Ernesto; et al. About a Formamide-Based Origin of Informational Polymers: Syntheses of Nucleobases and Favourable Thermodynamic Niches for Early Polymers. Origins of Life and Evolution of Biospheres. 2006, 36 (5–6): 523–531. Bibcode:2006OLEB...36..523S. PMID 17136429. doi:10.1007/s11084-006-9053-2. 
  6. ^ Sanchez, R. A.; Ferris, J. P.; Orgel, L. E. Studies in prebiotic synthesis. II. Synthesis of purine precursors and amino acids from aqueous hydrogen cyanide. Journal of Molecular Biology. 1967, 30 (2): 223–53. PMID 4297187. 
  7. ^ Ferris, J. P.; Orgel, L. E. Journal of the American Chemical Society 88 (5): 1074. 1966. doi:10.1021/ja00957a050. 
  8. ^ Ferris, J. P.; Kuder, J. E.; Catalano, O. W.; Kuder; Catalano. Photochemical Reactions and the Chemical Evolution of Purines and Nicotinamide Derivatives. Science. 1969, 166 (3906): 765–6. Bibcode:1969Sci...166..765F. PMID 4241847. doi:10.1126/science.166.3906.765. 
  9. ^ Oro, J.; Kamat, J. S.; Kamat. Amino-acid Synthesis from Hydrogen Cyanide under Possible Primitive Earth Conditions. Nature. 1961, 190 (4774): 442–3. Bibcode:1961Natur.190..442O. PMID 13731262. doi:10.1038/190442a0. 
  10. ^ Houben-Weyl, Vol . E5, p. 1547[需要完整来源]
  11. ^ Alfred Hassner, Irishi Namboothiri. Organic syntheses based on name reactions a practical guide to 750 transformations. Amsterdam: Elsevier. 2011-11-18. ISBN 978-0-080-96631-1. 
  1. ^ 本音是一声,在大陆作音译字时变调为四声,本义时仍为一声,在台湾通读一声
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