5,8-dihydropterin | 54099-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 5,8-dihydropterin
• 英文别名: 2-amino-5,8-dihydro-3H-pteridin-4-one；2-Amino-4-hydroxy-5,8-dihydropteridin；2-Amino-1,5-dihydropteridin-4-ol；2-amino-5,8-dihydro-3H-pteridin-4-one
• CAS: 54099-74-0
• 化学式: C₆H₇N₅O
• 分子量: 165.154
• InChiKey: UIHSXOMREQLGFW-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±52.0 °C(Predicted)
• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4-羟基蝶啶 、 羧基自由基 生成 5,8-dihydropterin
  参考文献：
  名称：

  Reactions of CO₂˙^–radicals with pterin and pterin-6-carboxylate ions

  摘要：

  Pulse radiolysis experiments showed that the reaction of pterin-6-carboxylate (Pn6CB) with CO2.- at pH 7 produced a monohydropterin radical similar to that observed for unsubstituted pterin (Pn), with the rate of the second order reaction for Pn6CB (k = 1.7 x 10(8) dm3 mol-1 s-1) being a factor of 2.5 slower than for Pn. At pH 10, where the 3,4-amide groups of the pterins were deprotonated, reactions of CO2.- with both pterins were too slow to be observed by this method. However, the fact that reactions occur on a slower time scale was established by the observation of products in gamma radiolysis experiments. Formation of these was followed by spectrophotometry and by measurement of CO2 yields. Over the entire pH range 6-10, titrations of Pn6CB with CO2.- led to a two-electron-equivalent reduction with no incorporation of CO2. Also the dihydro product was readily oxidised by air, a feature in which it resembled 5,8-dihydropterins reported elsewhere. With Pn at pH 7 there was again a two electron reduction with no incorporation of CO., but the product spectrum was completely different from that observed with Pn6CB. Furthermore, at pH 10 the stoichiometry of the titration indicated a four-electron-equivalent reduction, and a deficit in the CO2 yields demonstrated the incorporation of at least one CO2 per molecule. The spectrum and redox chemistry of this product strongly resembled those of tetrahydropterins. These effects of pH and the differences between Pn and Pn6CB were discussed and shown to be in accord with the known properties of di- and tetra-hydropterins.

  DOI：

  10.1039/p29910001687

文献信息

• Process For The Preparation Of Optically Pure Tetrahydropterins And Derivatives, And Specifically Of Optically Pure Tetrahydrofolic Acid And Derivatives Thereof, By Stereospecific Hydrogenation
  申请人：MULLER Hans Rudolf

  公开号：US20080306263A1

  公开（公告）日：2008-12-11

  Process for the preparation of tetrahydropterin and tetrahydropterin derivatives by hydrogenating pterin and pterin derivatives with hydrogen in the presence of a hydrogenating catalyst, in which the hydrogenation is carried out in a polar reaction medium and metal complexes that are soluble in the reaction medium are employed as the hydrogenation catalysts. The process is suited to the hydrogenation, particularly asymmetric hydrogenation, of folic acid, folio acid salts, folio acid esters, folio acid ester salts or dihydroforms thereof, with the proviso that in the event of using folic acid, carboxylic acid salts thereof or dihydroforms thereof the reaction medium is aqueous, and in the event of using folic acid esters, folic acid ester salts or dihydroforms thereof the reaction medium is an alcohol. The process opens up straightforward access to achiral and chiral pterin derivatives.

  通过在存在氢化催化剂的情况下，用氢气氢化葉酸和葉酸衍生物制备四氢生物葉酸和四氢生物葉酸衍生物的过程，其中氢化是在极性反应介质中进行的，并且可溶于反应介质的金属配合物被用作氢化催化剂。该过程适用于葉酸、葉酸盐、葉酸酯、葉酸酯盐或其二氢形式的氢化，特别是不对称氢化，但若使用葉酸、其羧酸盐或二氢形式，则反应介质为水，若使用葉酸酯、葉酸酯盐或其二氢形式，则反应介质为醇。该过程为得到无手性和手性葉酸衍生物提供了直接途径。
• Method for obtaining precursor Z and use thereof for the production of a means for therapy of human molybdenum cofactor deficiency
  申请人：Schwarz Guenter

  公开号：US20070037250A1

  公开（公告）日：2007-02-15

  The invention relates to a method for obtaining the molybdopterin derivative precursor Z, wherein an over-production of precursor Z occurs in host organisms by recombinant expression of precursor Z synthesizing proteins. The invention further relates to the use of precursor Z for the production of a means for the therapy of human molybdenum cofactor deficiency and associated diseases, which may be directly or indirectly attributed to an altered molybdenum cofactor synthesis, whereby precursor Z is used as essential component of said therapy means.
• US7504095B2
  申请人：——

  公开号：US7504095B2

  公开（公告）日：2009-03-17
• US7816525B1
  申请人：——

  公开号：US7816525B1

  公开（公告）日：2010-10-19
• Reactions of CO₂˙^–radicals with pterin and pterin-6-carboxylate ions
  作者：Mohsen Farahani、Parminder S. Surdhar、Scott Allen、David A. Armstrong、Christian Schöneich、Yun Mao、Klaus-Dieter Asmus

  DOI：10.1039/p29910001687

  日期：——

  Pulse radiolysis experiments showed that the reaction of pterin-6-carboxylate (Pn6CB) with CO2.- at pH 7 produced a monohydropterin radical similar to that observed for unsubstituted pterin (Pn), with the rate of the second order reaction for Pn6CB (k = 1.7 x 10(8) dm3 mol-1 s-1) being a factor of 2.5 slower than for Pn. At pH 10, where the 3,4-amide groups of the pterins were deprotonated, reactions of CO2.- with both pterins were too slow to be observed by this method. However, the fact that reactions occur on a slower time scale was established by the observation of products in gamma radiolysis experiments. Formation of these was followed by spectrophotometry and by measurement of CO2 yields. Over the entire pH range 6-10, titrations of Pn6CB with CO2.- led to a two-electron-equivalent reduction with no incorporation of CO2. Also the dihydro product was readily oxidised by air, a feature in which it resembled 5,8-dihydropterins reported elsewhere. With Pn at pH 7 there was again a two electron reduction with no incorporation of CO., but the product spectrum was completely different from that observed with Pn6CB. Furthermore, at pH 10 the stoichiometry of the titration indicated a four-electron-equivalent reduction, and a deficit in the CO2 yields demonstrated the incorporation of at least one CO2 per molecule. The spectrum and redox chemistry of this product strongly resembled those of tetrahydropterins. These effects of pH and the differences between Pn and Pn6CB were discussed and shown to be in accord with the known properties of di- and tetra-hydropterins.