β-D-galactopyranose-6-O-triphosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranose-6-O-triphosphate
• 英文别名: triphospho(-6)b-Gal；[hydroxy(phosphonooxy)phosphoryl] [(2R,3R,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl hydrogen phosphate
• 化学式: C₆H₁₅O₁₅P₃
• 分子量: 420.097
• InChiKey: NAVHMLAPOFQCLF-FPRJBGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  250
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  β-半乳糖苷酶 生成 β-D-galactopyranose-6-O-triphosphate
  参考文献：
  名称：

  Selective Diphosphorylation, Dithiodiphosphorylation, Triphosphorylation, and Trithiotriphosphorylation of Unprotected Carbohydrates and Nucleosides

  摘要：

  [GRAPHIC]Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylarting and triphosphitylating reagents to yield the corresponding polymer-bound cliphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodi phosphates, triphosphates, and trithiotriphosphates with high regioselectivity.

  DOI：

  10.1021/ol0521432

文献信息

• MODIFIED OLIGONUCLEOTIDES CONTAINING DIPHOSPHODIESTER INTERNUCLEOTIDE LINKAGES
  申请人：Parang Keykavous

  公开号：US20080207551A1

  公开（公告）日：2008-08-28

  The synthesis and biochemical utility of modified oligonucleotides containing diphosphodiester internucleotide linkages. The synthesis of these compounds was carried out using diphosphitylating reagents. Oligonucleotides containing diphosphate diester bridges wherein said oligonucleotides are synthesized via a solid-phase synthesis strategy to form modified oligonucleotides. Diphosphitylating, triphosphitylating, tetraphosphitylating, β-triphosphitylating, bifunctional diphosphitylating, bifunctional triphosphitylating, and bifunctional tetraphosphitylating reagents wherein, the phosphorus atoms are linked together through oxygen, sulfur, amino, or methylene groups and/or are substituted with chlorine, diisopropylamine and cyanoethoxy groups.

  含有二磷酸二酯间核苷酸连接的修饰寡核苷酸的合成和生物化学应用。这些化合物的合成是使用二磷酸化试剂进行的。通过固相合成策略合成含有二磷酸二酯桥的寡核苷酸来形成修饰寡核苷酸。其中，二磷酸化、三磷酸化、四磷酸化、β-三磷酸化、双官能团二磷酸化、双官能团三磷酸化和双官能团四磷酸化试剂中的磷原子通过氧、硫、氨基或亚甲基基团连接在一起，并且/或被氯、二异丙基胺和氰乙氧基基团取代。
• US8193384B2
  申请人：——

  公开号：US8193384B2

  公开（公告）日：2012-06-05
• [EN] MODIFIED OLIGONUCLEOTIDES CONTAINING DIPHOSPHODIESTER INTERNUCLEOTIDE LINKAGES<br/>[FR] OLIGONUCLEOTIDES MODIFIES CONTENANT DES LIAISONS INTERNUCLEOTIDIQUES DIPHOSPHODIESTER
  申请人：RHODE ISLAND EDUCATION

  公开号：WO2007030227A2

  公开（公告）日：2007-03-15

  [EN] The synthesis and biochemical utility of modified oligonucleotides containing diphosphodiester intermicleotide linkages. The synthesis of these compounds was carried out using diphosphirylating reagents. Oligonucleotides containing diphosphate diester bridges wherein said oligonucleotides are synthesized via a solid-phase synthesis strategy to form modified oligonucleotides. Diphosphitylating, triphosphitylating, tetraphosphitylating, ß-triphosphitylating, bifunctional diphosphitylating, bifunctional triphosphitylating, and bifunctional tetraphosphitylating reagents wherein, the phosphorus atoms are linked together through oxygen, sulfur, amino, or methylene groups and/or are substituted with chlorine, diisopropylamine and cyanoethoxy groups.
  [FR] La présente invention se rapporte à la synthèse et à l'utilité biochimique d'oligonucléotides modifiés contenant des liaisons internucléotidiques diphosphodiester. La synthèse desdits composés est effectuée à l'aide de réactifs de diphosphitylation. L'invention a également trait à des oligonucléotides contenant des ponts diester diphosphate, lesdits oligonucléotides étant synthétisés par le biais d'une technique de synthèse en phase solide permettant de former des oligonucléotides modifiés. L'invention concerne aussi des réactifs de diphosphitylation, de triphosphitylation, de tétraphosphitylation, de ß-triphosphitylation, de diphosphitylation bifonctionnelle, de triphosphitylation bifonctionnelle, et de tétraphosphitylation bifonctionnelle, dans lesquels des atomes de phosphore sont liés ensemble par l'intermédiaire de groupes oxygène, soufre, amino, ou méthylène, et/ou sont substitués par des groupes chlore, diisopropylamine et cyanoéthoxy.
• Selective Diphosphorylation, Dithiodiphosphorylation, Triphosphorylation, and Trithiotriphosphorylation of Unprotected Carbohydrates and Nucleosides
  作者：Yousef Ahmadibeni、Keykavous Parang

  DOI：10.1021/ol0521432

  日期：2005.12.1

  [GRAPHIC]Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylarting and triphosphitylating reagents to yield the corresponding polymer-bound cliphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodi phosphates, triphosphates, and trithiotriphosphates with high regioselectivity.